P
USRE36359EExpiredUtilityPatentIndex 71

Long chain carboxylic acid imide ester

Assignee: KURARAY COPriority: Apr 24, 1991Filed: May 1, 1997Granted: Oct 26, 1999
Est. expiryApr 24, 2011(expired)· nominal 20-yr term from priority
Inventors:EBASHI IWAOTAKIGAWA TETSUOINOUE MASAYASU
C07D 207/46C07D 209/48C07D 209/76C07D 211/94
71
PatentIndex Score
6
Cited by
44
References
32
Claims

Abstract

Provided is a long chain carboxylic acid imide ester (I) represented by the following general formula (I) ##STR1## wherein W is a divalent long chain hydrocarbon group which may optionally be interrupted by one or more groups each independently selected from the group consisting of an oxygen, atom, a sulfur atom, and a group of --N(R 1 )-- (R 1 being a lower alkyl group) and X represents a divalent hydrocarbon group which may optionally be substituted, or salt thereof. The above long chain carboxylic acid imide ester or its salts is useful for modifying enzymes or proteins having biological activities to give their derivatives which have, while retaining most of the original biological activities, an extremely prolonged plasma half-life as compared with the proteins and have no antigenecities and can be administered to animals.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A compound of the formula ##STR11## or a salt thereof, wherein W is a divalent long chain hydrocarbon radical having from 8 to 28 principal chain atoms; and wherein R 2 , R 3 , R 4  and R 5 , in combination with the carbon atoms to which they bond, form a benzene, cyclohexane, cyclopentane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]hepta-2-ene, 7-oxabicyclo[2.2.1]heptane or 7-oxabicyclo[2.2.1]hepta-2-ene ring system which is optionally substituted by --SO 3  H, --CO 2  H, --OH, F, Cl, Br, I, --CH 3  or --OCH 3 . 
     
     
       2. The compound according to claim 1, wherein the divalent hydrocarbon radical W has from 10 to 20 principal chain atoms. 
     
     
       3. The compound according to claim 2, wherein W is a divalent radical of the formula (CH 2 ) 10 , (CH 2 ) 11 , (CH 2 ) 12 , (CH 2 ) 13 , (CH 2 ) 14 , (CH 2 ) 15 , (CH 2 ) 16 , (CH 2 ) 17 , (CH 2 ) 18 , (CH 2 ) 19 , (CH 2 ) 20 , CH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 2  CH═CH(CH 2 ) 7 , (CH 2 ) 3  CH═CH(CH 2 ) 7 , (CH 2 ) 4  CH═CH(CH 2 ) 7 , (CH 2 ) 5  CH═CH(CH 2 ) 7 , (CH 2 ) 6  CH═CH(CH 2 ) 7 , (CH 2 ) 7  CH═CH(CH 2 ) 7 , (CH 2 ) 8  CH═CH(CH 2 ) 7 , (CH 2 ) 9  CH═CH(CH 2 ) 7 , (CH 2 ) 10  CH═CH(CH 2 ) 7 , (CH 2 ) 11  CH═CH(CH 2 ) 7 , (CH 2 ) 8  CH═CHCH 2 , (CH 2 ) 8  CH═CH(CH 2 ) 2 , (CH 2 ) 8  CH═CH(CH 2 ) 3 , (CH 2 ) 8  CH═CH(CH 2 ) 4 , (CH 2 ) 8  CH═CH(CH 2 ) 5 , (CH 2 ) 8  CH═CH(CH 2 ) 6 , (CH 2 ) 8  CH═CH(CH 2 ) 8 , (CH 2 ) 8  CH═CH(CH 2 ) 9 , (CH 2 ) 8  CH═CH(CH 2 ) 10 , CH 2  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 2  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 3  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 4  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 5  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 6  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 7  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 8  CH═CHCH 2  CH═CH(CH 2 ) 7 . 
     
     
       4. The compound according to claim 1, wherein ##STR12## is a radical of the formula ##STR13## 
     
     
       5. The compound according to claim 1, which is an alkali metal or alkaline earth metal salt. 
     
     
       6. The compound according to claim 1, which is N-(15-carboxypentadecanoyloxy)phthalimide. 
     
     
       7. The compound according to claim 1, which is N-(15-carboxypentadecanoyloxy)tetramethylphthalimide. 
     
     
       8. The compound according to claim 1, which is N-(15-carboxypentadecanoyloxy)-5-norbornene-2,3-dicarboximide. 
     
     
       9. A compound of the formula or a salt thereof, wherein W is a divalent long chain hydrocarbon radical having from 8 to 28 principal chain atoms; and wherein each of R 10 , R 11 , R 12 , R 13 , R 14  and R 15 , which can be the same or different, is a hydrogen atom; an alkyl radical; an aryl radical; an aralkyl radical; an --SO 3  H group; a radical of the formula --OH 6  wherein R 6  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical, an aralkyl radical and an acyl radical; a radical of the formula --NR 7  R 8  wherein each of R 7  and R 8 , which can be the same or different, is selected from the group consisting of an alkyl radical, an aryl radical, an aralkyl radical and an acyl radical; or a radical of the formula --CO 2  R 9  wherein R 9  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical or an aralkyl radical. 
     
     
       10. The compound according to claim 9, wherein the divalent hydrocarbon radical W has from 10 to 20 principal chain atoms. 
     
     
       11. The compound according to claim 10, wherein W is a divalent radical of the formula (CH 2 ) 10 , (CH 2 ) 11 , .[.(CH 2 ) 12  (CH 2 ) 13  (CH 2 ) 14 ,.]. .Iadd.(CH 2 ) 12 , (CH 2 ) 13 , (CH 2 ) 14 , .Iaddend.(CH 2 ) 15 , (CH 2 ) 16 , (CH 2 ) 17 , (CH 2 ) 18 , (CH 2 ) 19 , (CH 2 ) 20 , CH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 2  CH═CH(CH 2 ) 7 , (CH 2 ) 3  CH═CH(CH 2 ) 7 , (CH 2 ) 4  CH═CH(CH 2 ) 7 , (CH 2 ) 5  CH═CH(CH 2 ) 7 , (CH 2 ) 6  CH═CH(CH 2 ) 7 , (CH 2 ) 7  CH═CH(CH 2 ) 7 , (CH 2 ) 8  CH═CH(CH 2 ) 7 , (CH 2 ) 9  CH═CH(CH 2 ) 7 , (CH 2 ) 10  CH═CH(CH 2 ) 7 , (CH 2 ) 11  CH═CH(CH 2 ) 7 , (CH 2 ) 8  CH═CHCH 2 , (CH 2 ) 8  CH═CH(CH 2 ) 2 , (CH 2 ) 8  CH═CH(CH 2 ) 3 , (CH 2 ) 8  CH═CH(CH 2 ) 4 , (CH 2 ) 8  CH═CH(CH 2 ) 5 , (CH 2 ) 8  CH═CH(CH 2 ) 6 , (CH 2 ) 8  CH═CH(CH 2 ) 8 , (CH 2 ) 8  CH═CH(CH 2 ) 9 , (CH 2 ) 8  CH═CH(CH 2 ) 10 , CH 2  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 2  CH═CHCH 2  CH═CH(CH 2 ) 7 , .[.(CH 2 ) 3  CH═CHCH 2  CH═(CH 2 ) 7 ,.]. .Iadd.(CH 2 ) 3  CH═CHCH 2  CH═CH(CH 2 ) 7 , .Iaddend.(CH 2 ) 4  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 5  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 6  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 7  CH═CHCH 2  CH═CH(CH 2 ) 7 , or (CH 2 ) 8  CH═CHCH 2  CH═CH(CH 2 ) 7 . 
     
     
       12. The compound according to claim 9, wherein each of R 10 , R 11 , R 12 , R 13 , R 14  and R 15 , which can be the same or different, is hydrogen, methyl, ethyl, propyl, isopropyl, octadecyl, phenyl, p-bromophenyl, benzyl, p-methoxybenzyl, --SO 3  H, hydroxy, methoxy, ethoxy, propoxy, isopropoxy, phenoxy, p-bromophenoxy, benzyloxy, p-methoxybenzyloxy, acetoxy or benzoyloxy; or a radical of the formula --NR 7  R 8  selected from the group consisting of dimethylamino, diethylamino, N-methylacetamido and N-methylbenzamido; or a radical of the formula --CO 2  R 9  selected from the group consisting of carboxyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, phenoxycarbonyl and p-bromophenoxycarbonyl. 
     
     
       13. The compound according to claim 9, which is an alkali metal or alkaline earth metal salt. 
     
     
       14. The compound according to claim 9, which is N-(15-carboxypentadecanoyloxy)glutarimide. 
     
     
       15. A compound of the formula ##STR14## or a salt thereof, wherein W is a divalent long chain hydrocarbon radical interrupted by one or more groups each independently selected from the group consisting of an oxygen atom, a sulfur atom and an --N(R 1 )-- group wherein R 1  is lower alkyl, said radical W having from 8 to 28 principal chain atoms; and ##STR15## is a radical of the formula ##STR16## wherein each of R 2 , R 3 , R 4  and R 5 , which can be the same or different, is a hydrogen atom; an alkyl radical; an aryl radical; an aralkyl radical; an --SO 3  H group; a radical of the formula --OR 6  wherein R 6  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical, an aralkyl radical and an acyl radical; a radical of the formula --NR 7  R 8  wherein each of R 7  and R 8 , which can be the same or different, is selected from the group consisting of an alkyl radical, an aryl radical, an aralkyl radical and acyl radical; or a radical of the formula --CO 2  R 9  wherein R 9  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical and an aralkyl radical; or R 2 , R 3 , R 4  and R 5  can, in combination with the carbon atoms to which they bond, form a benzene, cyclohexane, cyclopentane, bicyclo [2.2.1]heptane, bicyclo[2.2.1]hepta-2-ene, 7-oxabicyclo[2.2.1]heptane or 7-oxabicyclo[2.2.1]hepta-2-ene ring system which is optionally substituted by --SO 3  H, --CO 2  H, --OH, F, Cl, Br, I, --CH 3  or --OCH 3  ; or R 2  and R 3  and/or R 4  and R 5 , in combination, can be a methylene or isopropylidene group; and each of R 10 , R 11 , R 12 , R 13 , R 14  and R 15 , which can be the same or different, is a hydrogen atom; an alkyl radical; an aryl radical; an aralkyl radical; an --SO 3  H group; a radical of the formula --OR 6  wherein R 6  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical, an aralkyl radical and an acyl radical; a radical of the formula --NR 7  R 8  wherein each of R 7  and R 8 , which can be the same or different, is selected from the group consisting of an alkyl radical, an aryl radical, an aralkyl radical and an acyl radical; or a radical of the formula --CO 2  R 9  wherein R 9  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical or an aralkyl radical. 
     
     
       16. The compound according to claim 15, wherein the divalent hydrocarbon radical W has from 10 to 20 principal chain atoms. 
     
     
       17. The compound according to claim 15, wherein R 1  is methyl, ethyl, propyl or isopropyl. 
     
     
       18. The compound according to claim 16, wherein W is a divalent radical of the formula (CH 2 ) 2  --O--(CH 2 ) 7 , (CH 2 ) 2  --O--(CH 2 ) 8 , (CH 2 ) 2  --O--(CH 2 ) 9 , (CH 2 ) 2  --O--(CH 2 ) 10 , (CH 2 ) 2  --O--(CH 2 ) 11 , (CH 2 ) 2  --O--(CH 2 ) 12 , (CH 2 ) 2  --O--(CH 2 ) 13 , (CH 2 ) 2  --O--(CH 2 ) 14 , (CH 2 ) 2  --O--(CH 2 ) 15 , (CH 2 ) 2  --O--(CH 2 ) 16 , (CH 2 ) 2  --O--(CH 2 ) 17 , (CH 2 ) 4  --O--(CH 2 ) 5 , (CH 2 ) 4  --O--(CH 2 ) 6 , (CH 2 ) 4  --O--(CH 2 ) 7 , .[.(CH 2 ) 4  --O--,(CH 2 ) 8  (CH 2 ) 4  --O--(CH 2 ) 9 ,.]. .Iadd.(CH 2 ) 3  --O--(CH 2 ) 8 , (CH 2 ) 4  --O--(CH 2 ) 9 , .Iaddend.(CH 2 ) 4  --O--(CH 2 ) 10 , (CH 2 ) 4  --O--(CH 2 ) 11 , (CH 2 ) 4  --O--(CH 2 ) 12 , (CH 2 ) 4  --O--(CH 2 ) 13 , (CH 2 ) 4  --O--(CH 2 ) 14 , (CH 2 ) 4  --O--(CH 2 ) 15 , (CH 2 ) 6  --O--(CH 2 ) 3 , (CH 2 ) 6  --O--(CH 2 ) 4 , (CH 2 ) 6  --O--(CH 2 ) 5 , (CH 2 ) 6  --O--(CH 2 ) 6 , (CH 2 ) 6  --O--(CH 2 ) 7 , (CH 2 ) 6  --O--(CH 2 ) 8 , (CH 2 ) 6  --O--(CH 2 ) 9 , (CH 2 ) 6  --O--(CH 2 ) 10 , (CH 2 ) 6  --O--(CH 2 ) 11 , (CH 2 ) 6  --O--(CH 2 ) 12 , (CH 2 ) 6  --O--(CH 2 ) 13 , (CH 2 ) 8  --O--CH 2 , (CH 2 ) 8  --O--(CH 2 ) 2 , (CH 2 ) 8  --O--(CH 2 ) 3 , (CH 2 ) 8  --O--(CH 2 ) 4 , (CH 2 ) 8  --O--(CH 2 ) 5 , (CH 2 ) 8  --O--(CH 2 ) 6 , (CH 2 ) 8  --O--(CH 2 ) 7 , (CH 2 ) 8  --O--(CH 2 ) 8 , (CH 2 ) 8  --O--(CH 2 ) 9 , (CH 2 ) 8  --O--(CH 2 ) 10 , (CH 2 ) 8  --O--(CH 2 ) 11 , (CH 2 ) 10  --O--CH 2 , (CH 2 ) 10  --O--(CH 2 ) 2 , (CH 2 ) 10  --O--(CH 2 ) 3 , (CH 2 ) 10  --O--(CH 2 ) 4 , (CH 2 ) 10  --O--(CH 2 ) 5 , (CH 2 ) 10  --O--(CH 2 ) 6 , (CH 2 ) 10  --O--(CH 2 ) 7 , (CH 2 ) 10  --O--(CH 2 ) 8 , (CH 2 ) 10  --O--(CH 2 ) 9 , (CH 2 ) 12  --O--CH 2 , (CH 2 ) 12  --O--(CH 2 ) 2 , (CH 2 ) 12  --O--(CH 2 ) 3 , (CH 2 ) 12  --O--(CH 2 ) 4 , (CH 2 ) 12  --O--(CH 2 ) 5 , (CH 2 ) 12  --O--(CH 2 ) 6 , (CH 2 ) 12  --O--(CH 2 ) 7 , CH 2  --O--(CH 2 ) 5  CH═CH(CH 2 ) 7 , (CH 2 ) 2  --O--(CH 2 ) 5  CH═CH(CH 2 ) 7 , (CH 2 ) 3  --O--(CH 2 ) 5  CH═CH(CH 2 ) 7 , (CH 2 ) 4  --O--(CH 2 ) 5  CH═CH(CH 2 ) 7 , or (CH 2 ) 5  --O--(CH 2 ) 5  CH═CH(CH 2 ) 7 . 
     
     
       19. The compound according to claim 16, wherein W is a divalent radical of the formula (CH 2 ) 2  --S--(CH 2 ) 7 , (CH 2 ) 2  --S--(CH 2 ) 8 , (CH 2 ) 2  --S--(CH 2 ) 9 , (CH 2 ) 2  --S--(CH 2 ) 10 , (CH 2 ) 2  --S--(CH 2 ) 11 , (CH 2 ) 2  --S--(CH 2 ) 12 , (CH 2 ) 2  --S--(CH 2 ) 13 , (CH 2 ) 2  --S--(CH 2 ) 14 , (CH 2 ) 2  --S--(CH 2 ) 15 , (CH 2 ) 2  --S--(CH 2 ) 16 , (CH 2 ) 2  --S--(CH 2 ) 17 , (CH 2 ) 4  --S--(CH 2 ) 5 , (CH 2 ) 4  --S--(CH 2 ) 6 , (CH 2 ) 4  --S--(CH 2 ) 7 , (CH 2 ) 4  --S--(CH 2 ) 8 , (CH 2 ) 4  --S--(CH 2 ) 9 , (CH 2 ) 4  --S--(CH 2 ) 10 , (CH 2 ) 4  --S--(CH 2 ) 11 , (CH 2 ) 4  --S--(CH 2 ) 12 , (CH 2 ) 4  --S--(CH 2 ) 13 , (CH 2 ) 4  --S--(CH 2 ) 14 , (CH 2 ) 4  --S--(CH 2 ) 15 , (CH 2 ) 6  --S--(CH 2 ) 3 , (CH 2 ) 6  --S--(CH 2 ) 4 , (CH 2 ) 6  --S--(CH 2 ) 5 , (CH 2 ) 6  --S--(CH 2 ) 6 , (CH 2 ) 6  --S--(CH 2 ) 7 , (CH 2 ) 6  --S--(CH 2 ) 8 , (CH 2 ) 6  --S--(CH 2 ) 9 , (CH 2 ) 6  --S--(CH 2 ) 10 , (CH 2 ) 6  --S--(CH 2 ) 11 , (CH 2 ) 6  --S--(CH 2 ) 12 , (CH 2 ) 6  --S--(CH 2 ) 13 , (CH 2 ) 8  --S--CH 2 , (CH 2 ) 8  --S--(CH 2 ) 2 , (CH 2 ) 8  --S--(CH 2 ) 3 , (CH 2 ) 8  --S--(CH 2 ) 4 , (CH 2 ) 8  --S--(CH 2 ) 5 , (CH 2 ) 8  --S--(CH 2 ) 6 , (CH 2 ) 8  --S--(CH 2 ) 7 , (CH 2 ) 8  --S--(CH 2 ) 8 , (CH 2 ) 8  --S--(CH 2 ) 9 , (CH 2 ) 8  --S--(CH 2 ) 10 , (CH 2 ) 8  --S--(CH 2 ) 11 , (CH 2 ) 10  --S--CH 2 , (CH 2 ) 10  --S--(CH 2 ) 2 , (CH 2 ) 10  --S--(CH 2 ) 3 , (CH 2 ) 10  --S--(CH 2 ) 4 , (CH 2 ) 10  --S--(CH 2 ) 5 , (CH 2 ) 10  --S--(CH 2 ) 6 , (CH 2 ) 10  --S--(CH 2 ) 7 , (CH 2 ) 10  --S--(CH 2 ) 8 , .[.(CH 2 ) 10  --S--(CH 2 ) 9 ),.]. .Iadd.(CH 2 ) 10  --S--(CH 2 ) 9 , .Iaddend.(CH 2 ) 12  --S--CH 2 , (CH 2 ) 12  --S--(CH 2 ) 2 , (CH 2 ) 12  --S--(CH 2 ) 3 , (CH 2 ) 12  --S--(CH 2 ) 4 , (CH 2 ) 12  --S--(CH 2 ) 5 , (CH 2 ) 12  --S--(CH 2 ) 6 , or (CH 2 ) 12  --S--(CH 2 ) 7 . 
     
     
       20. The compound according to claim 16, wherein W is a divalent radical of the formula (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 7 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 8 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 9 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 10 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 11 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 12 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 13 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 14 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 15 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 16 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 17 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 5 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 6 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 7 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 8 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 9 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 10 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 11 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 12 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 13 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 14 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 15 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 3 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 4 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 5 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 6 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 7 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 8 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 9 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 10 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 11 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 12 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 13 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 7 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 8 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 9 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 10 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 11 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 12 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 13 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 14 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 15 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 16 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 17 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 5 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 6 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 7 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 8 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 9 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 10 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 11 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 12 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 13 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 14 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 15 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 3 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 4 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 5 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 6 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 7 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 8 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 9 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 10 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 11 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 12 , or (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 13 . 
     
     
       21. The compound according to claim 16, wherein W is a divalent radical of the formula (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 4 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 5 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 6 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 7 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 8 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 9 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 10 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 11 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 12 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 13 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 14 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 2 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 3 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 4 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 5 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 6 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 7 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 8 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 9 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 10 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 11 , or (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 12 . 
     
     
       22. The compound according to claim 16, wherein W is a divalent radical of the formula (CH 2 ) 2  --S--S--(CH 2 ) 7 , (CH 2 ) 2  --S--S--(CH 2 ) 9 , (CH 2 ) 2  --S--S--(CH 2 ) 11 , (CH 2 ) 2  --S--S--(CH 2 ) 13 , (CH 2 ) 2  --S--S--(CH 2 ) 15 , (CH 2 ) 4  --S--S--(CH 2 ) 5 , (CH 2 ) 4  --S--S--(CH 2 ) 7 , (CH 2 ) 4  --S--S--(CH 2 ) 9 , (CH 2 ) 4  --S--S--(CH 2 ) 11 , (CH 2 ) 4  --S--S--(CH 2 ) 13 , (CH 2 ) 6  --S--S--(CH 2 ) 3 , (CH 2 ) 6  --S--S--(CH 2 ) 5 , (CH 2 ) 6  --S--S--(CH 2 ) 7 , (CH 2 ) 6  --S--S--(CH 2 ) 9 , (CH 2 ) 6  --S--S--(CH 2 ) 11 , (CH 2 ) 8  --S--S--CH 2 , (CH 2 ) 8  --S--S--(CH 2 ) 3 , (CH 2 ) 8  --S--S--(CH 2 ) 5 , (CH 2 ) 8  --S--S--(CH 2 ) 7 , or (CH 2 ) 8  --S--S--(CH 2 ) 9 . 
     
     
       23. The compound according to claim 15, wherein ##STR17## is a radical of the formula ##STR18## wherein each of R 2 , R 3 , R 4  and R 5 , which can be the same or different, is a hydrogen atom; an alkyl radical; an aryl radical; an aralkyl radical; an --SO 3  H group; a radical of the formula --OR 6  wherein R 6  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical, an aralkyl radical and an acyl radical; a radical of the formula --NR 7  R 8  wherein each of R 7  and R 8 , which can be the same or different, is selected from the group consisting of an alkyl radical, an aryl radical, an aralkyl radical and acyl radical; or a radical of the formula --CO 2  R 9  wherein R 9  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical and an aralkyl radical; or R 2 , R 3 , R 4  and R 5  can, in combination with the carbon atoms to which they bond, form a benzene, cyclohexane, cyclopentane, bicyclo [2.2.1]heptane, bicyclo[2.2.1]hepta-2-ene, 7-oxabicyclo[2.2.1]heptane or 7-oxabicyclo[2.2.1]hepta-2-ene ring system which is optionally substituted by --SO 3  H, --CO 2  H, --OH, F, Cl, Br, I, --CH 3  or --OCH 3  ; or R 2  and R 3  and/or R 4  and R 5 , in combination, can be a methylene or isopropylidene group. 
     
     
       24. The compound according to claim 23, wherein R 2 , R 3 , R 4  and R 5 , in combination with the carbon atoms to which they bond, form a benzene, cyclohexane, cyclopentane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]hepta-2-ene, 7-oxabicyclo[2.2.1]heptane or 7-oxabicyclo[2.2.1]hepta-2-ene ring system which is optionally substituted by --SO 3  H, --CO 2  H, --OH, F, Cl, Br, I, --CH 3  or --OCH 3 . 
     
     
       25. The compound according to claim 23, wherein each of R 2 , R 3 , R 4  and R 5 , which can be the same or different, is hydrogen, methyl, ethyl, propyl, isopropyl, octadecyl, phenyl, p-bromophenyl, benzyl, p-methoxybenzyl, --SO 3  H, hydroxy, methoxy, ethoxy, propoxy, isopropoxy, phenoxy, p-bromophenoxy, benzyloxy, p-methoxybenzyloxy, acetoxy or benzoyloxy; or a radical of the formula --NR 7  R 8  selected from the group consisting of dimethylamino, diethylamino, N-methylacetamido and N-methylbenzamido; or a radical of the formula --CO 2  R 9  selected from the group consisting of carboxyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, phenoxycarbonyl and p-bromophenoxycarbonyl. 
     
     
       26. The compound according to claim 23, wherein R 2  and R 3  and/or R 4  and R 5 , in combination, form a methylene or isopropylidene group. 
     
     
       27. The compound according to claim 26, wherein ##STR19## is a radical of the formula ##STR20## 
     
     
       28. The compound according to claim 24, wherein is a radical of the formula ##STR21## 
     
     
       29. The compound according to claim 15, wherein is a radical of the formula ##STR22## wherein each of R 10 , R 11 , R 12 , R 13 , R 14  and R 15 , which can be the same or different, is a hydrogen atom; an alkyl radical; an aryl radical; an aralkyl radical; an --SO 3  H group; a radical of the formula --OR 6  wherein R 6  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical, an aralkyl radical and an acyl radical; a radical of the formula --NR 7  R 8  wherein each of R 7  and R 8 , which can be the same or different, is selected from the group consisting of an alkyl radical, an aryl radical, an aralkyl radical and an acyl radical; or a radical of the formula --CO 2  R 9  wherein R 9  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical or an aralkyl radical. 
     
     
       30. The compound according to claim 29, wherein each of R 10 , R 11 , R 12 , R 13 , R 14  and R 15 , which can be the same or different, is hydrogen, methyl, ethyl, propyl, isopropyl, octadecyl, phenyl, p-bromophenyl, benzyl, p-methoxybenzyl, --SO 3  H, hydroxy, methoxy, ethoxy, propoxy, isopropoxy, phenoxy, p-bromophenoxy, benzyloxy, p-methoxybenzyloxy, acetoxy or benzoyloxy; or a radical of the formula --NR 7  R 8  selected from the group consisting of dimethylamino, diethylamino, N-methylacetamido and N-methylbenzamido; or a radical of the formula --CO 2  R 9  selected from the group consisting of carboxyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, phenoxycarbonyl and p-bromophenoxycarbonyl. 
     
     
       31. The compound according to claim 15, which is an alkali metal or alkaline earth metal salt. .Iadd. 
     
     
       32.  A protein compound having the formula   (protein)(Z).sub.n     wherein (protein) represents a pharmacologically active protein having n amino radicals each derivable from an amino group by removal of one of its hydrogen atoms, and (Z) is a radical of a long chain carboxylic acid having the formula ##STR23## wherein W is a divalent long chain hydrocarbon radical which is uninterrupted or interrupted by one or more groups each independently selected from the group consisting of an oxygen atom, a sulfur atom and an --N(R 1 ) group wherein R 1  is lower alkyl, said radical W having from 8 to 28 principal chain atoms, each (Z) being derivable from a long chain dicarboxylic acid HO 2  C--W--CO 2  H by removal of a hydroxyl group from one of its carbonyl groups, each (Z) being bonded to one of said n amino radicals in the protein, n being an average of the number of amide bonds between (Z) and (protein) and being a number from 1 to 8. .Iaddend..Iadd.33. A protein compound according to claim 32, wherein the divalent radical W has from 10 to 20 principal chain atoms.   
     
     
        .Iaddend..Iadd.4.  A protein compound according to claim 32, wherein R 1  is methyl, ethyl, propyl or isopropyl. .Iaddend..Iadd.35. A protein compound according to claim 33, wherein W is a divalent radical of the formula (CH 2 ) 10 , (CH 2 ) 11 , (CH 2 ) 13 , (CH 2 ) 14 , (CH 2 ) 15 , (CH 2 ) 16 , (CH 2 ) 17 , (CH 2 ) 18 , (CH 2 ) 19 , (CH 2 ) 20 , CH 2  CH--CH(CH 2 ) 7 , (CH 2 ) 2  CH═CH(CH 2 ) 7 , (CH 2 ) 3  CH═CH(CH 2 ) 7 , (CH 2 ) 4  CH═CH(CH 2 ) 7 , (CH 2 ) 5  CH═CH(CH 2 ) 7 , (CH 2 ) 6  CH═CH(CH 2 ) 7 , (CH 2 ) 7  CH═CH(CH 2 ) 7 , (CH 2 ) 8  CH═CH(CH 2 ) 7 , (CH 2 ) 9  CH═CH(CH 2 ) 7 , (CH 2 ) 10  CH═CH(CH 2 ) 7 , (CH 2 ) 11  CH═CH(CH 2 ) 7 , (CH 2 ) 8  CH═CHCH 2 , (CH 2 ) 8  CH═CH(CH 2 ) 2 , (CH 2 ) 8  CH═CH(CH 2 ) 3 , (CH 2 ) 8  CH═CH(CH 2 ) 4 , (CH 2 ) 8  CH═CH(CH 2 ) 5 , (CH 2 ) 8  CH═CH(CH 2 ) 6 , (CH 2 ) 8  CH═CH(CH 2 ) 8 , (CH 2 ) 8  CH═CH(CH 2 ) 9 , (CH 2 ) 8  CH═CH(CH 2 ) 10 , CH 2  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 2  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 3  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 4  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 5  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 6  CH═CHCH 2  CH═CH(CH 2 ) 7 , (CH 2 ) 7  CH═CHCH 2  CH═CH(CH 2 ) 7 , or (CH 2 ) 8  CH═CHCH 2  CH═CH(CH 2 ) 7 . .Iaddend..Iadd.36. A protein compound according to claim 35, wherein W is a divalent group of the formula (CH 2 ) 12 , (CH 2 ) 14 , (CH 2 ) 16 , (CH 2 ) 18   
     
     
        or (CH 2 ) 20 . .Iaddend..Iadd.37.  A protein compound according to claim 33, wherein W is a divalent radical of the formula (CH 2 ) 2  --O--(CH 2 ) 7 , (CH 2 ) 2  --O--(CH 2 ) 8 , (CH 2 ) 2  --O--(CH 2 ) 9 , (CH 2 ) 2  --O--(CH 2 ) 10 , (CH 2 ) 2  --O--(CH 2 ) 11 , (CH 2 ) 2  --O--(CH 2 ) 12 , (CH 2 ) 2  --O--(CH 2 ) 13 , (CH 2 ) 2  --O--(CH 2 ) 14 , (CH 2 ) 2  --O--(CH 2 ) 15 , (CH 2 ) 2  --O--(CH 2 ) 16 , (CH 2 ) 2  --O--(CH 2 ) 17 , (CH 2 ) 4  --O--(CH 2 ) 5 , (CH 2 ) 4  --O--(CH 2 ) 6 , (CH 2 ) 4  --O--(CH 2 ) 7 , (CH 2 ) 4  --O--(CH 2 ) 8 , (CH 2 ) 4  --O--(CH 2 ) 9 , (CH 2 ) 4  --O--(CH 2 ) 10 , (CH 2 ) 4  --O--(CH 2 ) 11 , (CH 2 ) 4  --O--(CH 2 ) 12 , (CH 2 ) 4  --O--(CH 2 ) 13 , (CH 2 ) 4  --O--(CH 2 ) 14 , (CH 2 ) 4  --O--(CH 2 ) 15 , (CH 2 ) 6  --O--(CH 2 ) 3 , (CH 2 ) 6  --O--(CH 2 ) 4 , (CH 2 ) 6  --O--(CH 2 ) 5 , (CH 2 ) 6  --O--(CH 2 ) 6 , (CH 2 ) 6  --O--(CH 2 ) 7 , (CH 2 ) 6  --O--(CH 2 ) 8 , (CH 2 ) 6  --O--(CH 2 ) 9 , (CH 2 ) 6  --O--(CH 2 ) 10 , (CH 2 ) 6  --O--(CH 2 ) 11 , (CH 2 ) 6  --O--(CH 2 ) 12 , (CH 2 ) 6  --O--(CH 2 ) 13 , (CH 2 ) 8  --O--CH 2 , (CH 2 ) 8  --O--(CH 2 ) 2 , (CH 2 ) 8  --O--(CH 2 ) 3 , (CH 2 ) 8  --O--(CH 2 ) 4 , (CH 2 ) 8  --O--(CH 2 ) 5 , (CH 2 ) 8  --O--(CH 2 ) 6 , (CH 2 ) 8  --O--(CH 2 ) 7 , (CH 2 ) 8  --O--(CH 2 ) 8 , (CH 2 ) 8  --O--(CH 2 ) 9 , (CH 2 ) 8  --O--(CH 2 ) 10 , (CH 2 ) 8  --O--(CH 2 ) 11 , (CH 2 ) 10  --O--CH 2 , (CH 2 ) 10  --O--(CH 2 ) 2 , (CH 2 ) 10  --O--(CH 2 ) 3 , (CH 2 ) 10  --O--(CH 2 ) 4 , (CH 2 ) 10  --O--(CH 2 ) 5 , (CH 2 ) 10  --O--(CH 2 ) 6 , (CH 2 ) 10  --O--(CH 2 ) 7 , (CH 2 ) 10  --O--(CH 2 ) 8 , (CH 2 ) 10  --O--(CH 2 ) 9 , (CH 2 ) 12  --O--CH 2 , (CH 2 ) 12  --O--(CH 2 ) 2 , (CH 2 ) 12  --O--(CH 2 ) 3 , (CH 2 ) 12  --O--(CH 2 ) 4 , (CH 2 ) 12  --O--(CH 2 ) 5 , (CH 2 ) 12  --O--(CH 2 ) 6 , (CH 2 ) 12  --O--(CH 2 ) 7 , CH 2  --O--(CH 2 ) 5  CH═CH(CH 2 ) 7 , (CH 2 ) 2  --O--(CH 2 ) 5  CH═CH(CH 2 ) 7 , (CH 2 ) 3  --O--(CH 2 ) 5  CH═CH(CH 2 ) 7 , (CH 2 ) 4  --O--(CH 2 ) 5  CH═CH(CH 2 ) 7 , or (CH 2 ) 5  --O--(CH 2 ) 5   
     
     
        CH═CH(CH 2 ) 7 . .Iaddend..Iadd.38.  A protein compound according to claim 33, wherein W is a divalent radical of the formula (CH 2 ) 2  --S--(CH 2 ) 7 , (CH 2 ) 2  --S--(CH 2 ) 8 , (CH 2 ) 2  --S--(CH 2 ) 9 , (CH 2 ) 2  --S--(CH 2 ) 10 , (CH 2 ) 2  --S--(CH 2 ) 11 , (CH 2 ) 2  --S--(CH 2 ) 12 , (CH 2 ) 2  --S--(CH 2 ) 13 , (CH 2 ) 2  --S--(CH 2 ) 14 , (CH 2 ) 2  --S--(CH 2 ) 15 , (CH 2 ) 2  --S--(CH 2 ) 16 , (CH 2 ) 2  --S--(CH 2 ) 17 , (CH 2 ) 4  --S--(CH 2 ) 5 , (CH 2 ) 4  --S--(CH 2 ) 6 , (CH 2 ) 4  --S--(CH 2 ) 7 , (CH 2 ) 4  --S--(CH 2 ) 8 , (CH 2 ) 4  --S--(CH 2 ) 9 , (CH 2 ) 4  --S--(CH 2 ) 10 , (CH 2 ) 4  --S--(CH 2 ) 11 , (CH 2 ) 4  --S--(CH 2 ) 12 , (CH 2 ) 4  --S--(CH 2 ) 13 , (CH 2 ) 4  --S--(CH 2 ) 14 , (CH 2 ) 4  --S--(CH 2 ) 15 , (CH 2 ) 6  --S--(CH 2 ) 3 , (CH 2 ) 6  --S--(CH 2 ) 4 , (CH 2 ) 6  --S--(CH 2 ) 5 , (CH 2 ) 6  --S--(CH 2 ) 6 , (CH 2 ) 6  --S--(CH 2 ) 7 , (CH 2 ) 6  --S--(CH 2 ) 8 , (CH 2 ) 6  --S--(CH 2 ) 9 , (CH 2 ) 6  --S--(CH 2 ) 10 , (CH 2 ) 6  --S--(CH 2 ) 11 , (CH 2 ) 6  --S--(CH 2 ) 12 , (CH 2 ) 6  --S--(CH 2 ) 13 , (CH 2 ) 8  --S--CH 2 , (CH 2 ) 8  --S--(CH 2 ) 2 , (CH 2 ) 8  --S--(CH 2 ) 3 , (CH 2 ) 8  --S--(CH 2 ) 4 , (CH 2 ) 8  --S--(CH 2 ) 5 , (CH 2 ) 8  --S--(CH 2 ) 6 , (CH 2 ) 8  --S--(CH 2 ) 7 , (CH 2 ) 8  --S--(CH 2 ) 8 , (CH 2 ) 8  --S--(CH 2 ) 9 , (CH 2 ) 8  --S--(CH 2 ) 10 , (CH 2 ) 8  --S--(CH 2 ) 11 , (CH 2 ) 10  --S--CH 2 , (CH 2 ) 10  --S--(CH 2 ) 2 , (CH 2 ) 10  --S--(CH 2 ) 3 , (CH 2 ) 10  --S--(CH 2 ) 4 , (CH 2 ) 10  --S--(CH 2 ) 5 , (CH 2 ) 10  --S--(CH 2 ) 6 , (CH 2 ) 10  --S--(CH 2 ) 7 , (CH 2 ) 10  --S--(CH 2 ) 8 , (CH 2 ) 10  --S--(CH 2 ) 9 , (CH 2 ) 12  --S--CH 2 , (CH 2 ) 12  --S--(CH 2 ) 2 , (CH 2 ) 12  --S--(CH 2 ) 3 , (CH 2 ) 12  --S--(CH 2 ) 4 , (CH 2 ) 12  --S--(CH 2 ) 5 , (CH 2 ) 12  --S--(CH 2 ) 6 , or (CH 2 ) 12  --S--(CH 2 ) 7 . .Iaddend..Iadd.39. A protein compound according to claim 33, wherein W is a divalent radical of the formula (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 7 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 8 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 9 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 10 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 11 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 12 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 13 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 14 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 15 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 16 , (CH 2 ) 2  --N(CH 3 )--(CH 2 ) 17 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 5 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 6 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 7 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 8 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 9 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 10 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 11 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 12 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 13 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 14 , (CH 2 ) 4  --N(CH 3 )--(CH 2 ) 15 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 3 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 4 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 5 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 6 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 7 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 8 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 9 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 10 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 11 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 12 , (CH 2 ) 6  --N(CH 3 )--(CH 2 ) 13 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 7 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 8 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 9 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 10 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 11 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 12 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 13 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 14 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 15 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 16 , (CH 2 ) 2  --N(C 2  H 5 )--(CH 2 ) 17 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 5 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 6 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 7 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 8 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 9 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 10 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 11 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 12 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 13 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 14 , (CH 2 ) 4  --N(C 2  H 5 )--(CH 2 ) 15 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 3 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 4 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 5 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 6 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 7 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 8 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 9 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 10 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 11 , (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 12 , or (CH 2 ) 6  --N(C 2  H 5 )--(CH 2 ) 13 . .Iaddend..Iadd.40. A protein compound according to claim 33, wherein W is a divalent radical of the formula (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 4 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 5 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 6 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 7 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 8 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 9 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 10 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 11 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 12 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 13 , (CH 2 ) 2  --O--(CH 2 ) 2  --O--(CH 2 ) 14 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 2 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 3 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 4 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 5 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 6 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 7 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 8 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 9 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 10 , (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 11 , or (CH 2 ) 4  --O--(CH 2 ) 2  --O--(CH 2 ) 12 . .Iaddend..Iadd.41. A protein compound according to claim 33, wherein W is a divalent radical of the formula (CH 2 ) 2  --S--S--(CH 2 ) 7 , (CH 2 ) 2  --S--S--(CH 2 ) 9 , (CH 2 ) 2  --S--S--(CH 2 ) 11 , (CH 2 ) 2  --S--S--(CH 2 ) 13 , (CH 2 ) 2  --S--S--(CH 2 ) 15 , (CH 2 ) 4  --S--S--(CH 2 ) 5 , (CH 2 ) 4  --S--S--(CH 2 ) 7 , (CH 2 ) 4  --S--S--(CH 2 ) 9 , (CH 2 ) 4  --S--S--(CH 2 ) 11 , (CH 2 ) 4  --S--S--(CH 2 ) 13 , (CH 2 ) 6  --S--S--(CH 2 ) 3 , (CH 2 ) 6  --S--S--(CH 2 ) 5 , (CH 2 ) 6  --S--S--(CH 2 ) 7 , (CH 2 ) 6  --S--S--(CH 2 ) 9 , (CH 2 ) 6  --S--S--(CH 2 ) 11 , (CH 2 ) 8  --S--S--CH 2 , (CH 2 ) 8  --S--S--(CH 2 ) 3 , (CH 2 ) 8  --S--S--(CH 2 ) 5 , (CH 2 ) 8  --S--S--(CH 2 ) 7 , or (CH 2 ) 8  --S--S--(CH 2 ) 9 . .Iaddend..Iadd.42. A protein compound according to claim 32 wherein said pharmacologically active protein is asparaginase arginase, interleukin-1, interleukin-2, interleukin-3, interleukin-4, interleukin-5, interleukin-6, interleukin-7, interleukin-8, urokinase, prourokinase, streptokinase, tissue plasminogen activator, β-glucosidase, β-glucuronidase, α-galactosidase deaminase, uricase, superoxide dismutase, insulin, bilirubin oxidase, granolocyte colony-stimulating factor, granolocyte macrophage colony-stimulating factor, macrophage colony-stimulating factor, neocarzinostatin, catalase, elastase, erythropoietin, interferon-α, interferon-β, interferon-γ, tumor necrosis factor-α, tumor necrosis factor-β, nerve growth factor, epidermal growth factor, ovalbumin, platelet derived growth factor, thrombomodulin, α antitrypsin, bone morphogenetic protein, cartilage derived factor, fibroblast growth factor, growth hormone, transforming growth factor-β, blood coagulation factor IX, protein C, protein S, insulin-like growth factor, calcitonin, somatostatin, tissue inhibitor of metalloproteinase, atrial natriuretic hormone, CD-4 protein cystatin, calpastatin, urinastatin or parathyroid hormone. .Iaddend..Iadd.43. A protein compound according to claim 42, wherein W is a divalent radical of the formula (CH 2 ) 12 , (CH 2 ) 14 , (CH 2 ) 16 , (CH 2 ) 18  or (CH 2 ) 20 . .Iaddend..Iadd.44. A protein compound according to claim 43, wherein said pharmacologically active protein is superoxide dismutase. .Iaddend..Iadd.45. A protein compound according to claim 44, wherein W is (CH 2 ) 12 . .Iaddend..Iadd.46. The protein compound according to claim 45, wherein n is 3.6. .Iaddend..Iadd.47. The protein compound according to claim 45, wherein n is 4.4. .Iaddend..Iadd.48. The protein compound according to claim 45, wherein n is 5.4. .Iaddend..Iadd.49. A protein compound according to claim 44, wherein W is (CH 2 ) 16 . .Iaddend..Iadd.50. The protein compound according to claim 49, wherein n is 2.0. .Iaddend..Iadd.51. A protein compound according to claim 44, wherein W is (CH 2 ) 18 . 
     
     
        .Iaddend..Iadd.52.  The protein compound according to claim 51, wherein n is 2.0. .Iaddend..Iadd.53. A protein compound according to claim 43, wherein said pharmacologically active protein is neocarzinostatin. .Iaddend..Iadd.54. A protein compound according to claim 53, wherein W is (CH 2 ) 14 . .Iaddend..Iadd.55. The protein compound according to claim 54, having no free amino groups. .Iaddend..Iadd.56. A protein compound according to claim 53, wherein W is (CH 2 ) 16 . .Iaddend..Iadd.57. The protein compound according to claim 56, having no free amino groups. .Iaddend..Iadd.58. A process for preparing a protein compound having the formula   (protein)(Z).sub.n     wherein (protein) represents a pharmacologically active protein having n amino radicals each derivable from an amino group by removal of one of its hydrogen atoms, and (Z) is a radical of a long chain carboxylic acid having the formula ##STR24## wherein W is a divalent long chain hydrocarbon radical which is uninterrupted or interrupted by one or more groups each independently selected from the group consisting of an oxygen atom, a sulfur atom and a --N(R 1 ) group wherein R 1  is lower alkyl, said radical W having from 8 to 28 principal chain atoms, each (Z) being derivable from a long-chain dicarboxylic acid HO 2  C--W--CO 2  H by removal of a hydroxyl group from one of its carbonyl groups, each (Z) being bonded to one of said n amino radicals in said protein, n being an average of the number of amide bonds between (Z) and (protein) and being a number from 1 to 8, said process comprising reacting a compound of the formula: ##STR25## or a salt thereof, wherein W is defined as above and ##STR26## is a radical of the formula ##STR27## wherein each of R 2 , R 3 , R 4  and R 5 , which are the same or different, is a hydrogen atom; an alkyl radical; an aryl radical; an aralkyl radical; an --SO 3  H group; a radical of the formula --OR 6  wherein R 6  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical, an aralkyl radical and an acyl radical; a radical of the formula --NR 7  R 8  wherein each of R 7  and R 8 , which are the same or different, is selected from the group consisting of an alkyl radical, an aryl radical, an aralkyl radical and an acyl radical; or a radical of the formula --CO 2  R 9  wherein R 9  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical and an aralkyl radical; or R 2 , R 3 , R 4  and R 5  in combination with the carbon atoms to which they bond, form a benzene, cyclohexane, cyclopentane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]hepta-2-ene, 7-oxabicyclo[2.2.1]heptane or 7-oxabicyclo[2.2.1]hepta-2-ene ring system which is unsubstituted or substituted by --SO 3  H, --CO 2  H, --OH, F, Cl, Br, I, --CH 3  or --OCH 3  ; or R 2  and R 3 , R 4  and R 5 , or both, in combination, are a methylene or isopropylidene group; and each of R 10 , R 11 , R 12 , R 13 , R 14  and R 15 , which are the same or different, is a hydrogen atom; an alkyl radical; an aryl radical; an aralkyl radical; an --SO 3  H group; a radical of the formula --OR 6  wherein R 6  is selected from the group consisting of a hydrogen atom, an alkyl radical; an aryl radical, an aralkyl radical and an acyl radical; a radical of the formula --NR 7  R 8  wherein each of R 7  and R 8 , which are the same or different, is selected from the group consisting of an alkyl radical, an aryl radical, an aralkyl radical and an aryl radical; or a radical of the formula --CO 2  R 9  wherein R 9  is selected from the group consisting of a hydrogen atom, an alkyl radical, an aryl radical or an aralkyl radical;   with a pharmaceutically active protein defined as above in an aqueous solution at a pH maintained within the range of 6 to 10, at a reaction temperature of from about 3° to 50° C. which does not exceed the denaturation temperature of the protein;   followed by separating the resultant protein compound from the reaction   
     
     
        medium. .Iaddend..Iadd.59.  A process according to claim 58, wherein the pharmacologically active protein starting material is asparaginase, arginase, interleukin-1, interleukin-2, interleukin-3, interleukin-4, interleukin-5, interleukin-6, interleukin-7, interleukin-8, urokinase, prourokinase, streptokinase, tissue plasminogen activator, β-glucosidase, β-glucuronidase, α-galactosidase, adenosine deaminase, uricase, superoxide dismutase, insulin, bilirubin oxidase, granolocyte colony-stimulating factor, granolocyte macrophage colony-stimulating factor, macrophage colony-stimulating factor, neocarzinostatin, catalase, elastase, erythropoietin, interferon-α, interferon-β, interferon-γ, tumor necrosis factor-α, tumor necrosis factor-β, nerve growth factor, epidermal growth factor, ovalbumin, platelet derived growth factor, thrombomodulin, α-antitrypsin, bone morphogenetic protein, cartilage derived factor, fibroblast growth factor, growth hormone, transforming growth factor-β, blood coagulation factor IX, protein C, protein S, insulin-like growth factor, calcitonin, somatostatin, tissue inhibitor of metalloproteinase, atrial natriuretic hormone, CD-4 protein, cystatin, calpastatin, urinastatin or parathyroid hormone. .Iaddend..Iadd.60. A process according to claim 58, wherein the starting material of formula (II) is: N-(13-carboxytridecanoyloxy)succinimide;   N-(15-carboxypentadecanoyloxy)succinimide;   N-(17-carboxyheptadecanoyloxy)succinimide;   N-(19-carboxynonadecanoyloxy)succinimide;   N-(21-carboxyheneicosanoyloxy)succinimide;   N-(15-carboxypentadecanoyloxy)phthalimide;   N-(15-carboxypentadecanoyloxy)tetramethylphthalimide;   N-(15-carboxypentadecanoyloxy)5-norbornene-2,3-dicarboximide;   N-(15-carboxypentadecanoyloxy)tartrimide;   N-(13-carboxytridecanoyloxy)sulfosuccinimide sodium salt;   N-(15-carboxypentadecanoyloxy)-3-isopropylsuccinimide;   N-(15-carboxypentadecanoyloxy)tetramethylsuccinimide;   N-(15-carboxypentadecanoyloxy)-3-benzylsuccinimide;   N-(15-carboxypentadecanoyloxy)itaconimide; or   
     
     
       N-(15-carboxypentadecanoyloxy)glutarimide. .Iaddend..Iadd.61.  A process according to claim 59, wherein the starting material of formula (II) is: N-(13-carboxytridecanoyloxy)succinimide;   N-(15-carboxypentadecanoyloxy)succinimide;   N-(17-carboxyheptadecanoyloxy)succinimide;   N-(19-carboxynonadecanoyloxy)succinimide;   N-(21-carboxyheneicosanoyloxy)succinimide;   N-(15-carboxypentadecanoyloxy)phthalimide;   N-(15-carboxypentadecanoyloxy)tetramethylphthalimide;   N-(15-carboxypentadecanoyloxy)5-norbornene-2,3-dicarboximide;   N-(15-carboxypentadecanoyloxy)tartrimide;   N-(13-carboxytridecanoyloxy)sulfosuccinimide sodium salt;   N-(15-carboxypentadecanoyloxy)-3-isopropylsuccinimide;   N-(15-carboxypentadecanoyloxy)tetramethylsuccinimide;   N-(15-carboxypentadecanoyloxy)-3-benzylsuccinimide;   N-(15-carboxypentadecanoyloxy)itaconimide; or   
     
     
       N-(15-carboxypentadecanoyloxy)glutarimide. .Iaddend..Iadd.62.  A process according to claim 61, wherein the pharmacologically active protein starting material is superoxide dismutase and the starting material of formula (II) is N-(13-carboxytridecanoyloxy)succinimide. .Iaddend..Iadd.63. A compound according to claim 61, wherein the pharmacologically active protein starting material is superoxide dismutase and the starting material of formula (II) is N-(17-carboxyheptadecanoyloxy)succinimide. .Iaddend..Iadd.64. A process according to claim 61, wherein the pharmacologically active protein starting material is superoxide dismutase and the starting material of formula (II) is N-(19-carboxynonadecanoyloxy)succinimide. .Iaddend..Iadd.65. A process according to claim 61, wherein the pharmacologically active protein starting material is neocarzinostatin and the starting material of formula (II) is N-(15-carboxypentadecanoyloxy)succinimide. .Iaddend..Iadd.66. A process according to claim 61, wherein the pharmacologically active protein starting material is neocarzinostatin and the starting material of formula (II) is N-(17-carboxyheptadecanoyloxy)succinimide. .Iaddend.

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