FI63015C - Foerfarande foer framstaellning av terapeutiskt aktiva di-n-propylmetylaminderivat - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiva di-n-propylmetylaminderivat Download PDFInfo
- Publication number
- FI63015C FI63015C FI771780A FI771780A FI63015C FI 63015 C FI63015 C FI 63015C FI 771780 A FI771780 A FI 771780A FI 771780 A FI771780 A FI 771780A FI 63015 C FI63015 C FI 63015C
- Authority
- FI
- Finland
- Prior art keywords
- propyl
- butylamine
- compounds
- compound
- methyl
- Prior art date
Links
- 230000004913 activation Effects 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 75
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 229960003805 amantadine Drugs 0.000 description 19
- 238000000034 method Methods 0.000 description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 238000007792 addition Methods 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 208000018737 Parkinson disease Diseases 0.000 description 8
- 206010007776 catatonia Diseases 0.000 description 8
- 150000003956 methylamines Chemical class 0.000 description 8
- 239000003176 neuroleptic agent Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N fumaric acid group Chemical group C(\C=C\C(=O)O)(=O)O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 102000010909 Monoamine Oxidase Human genes 0.000 description 5
- 108010062431 Monoamine oxidase Proteins 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 4
- PWBPWDVACUYDGH-UHFFFAOYSA-N 4-propyl-n-prop-2-ynylheptan-4-amine Chemical compound CCCC(CCC)(CCC)NCC#C PWBPWDVACUYDGH-UHFFFAOYSA-N 0.000 description 4
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 4
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000003291 dopaminomimetic effect Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- IOHZJCCMJGFCGF-UHFFFAOYSA-N n,n-dimethyl-4-propylheptan-4-amine Chemical compound CCCC(CCC)(CCC)N(C)C IOHZJCCMJGFCGF-UHFFFAOYSA-N 0.000 description 4
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 4
- 229960003147 reserpine Drugs 0.000 description 4
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- KVMSHRYFLBDXSZ-UHFFFAOYSA-N 4-propyl-n,n-bis(prop-2-ynyl)heptan-4-amine Chemical compound CCCC(CCC)(CCC)N(CC#C)CC#C KVMSHRYFLBDXSZ-UHFFFAOYSA-N 0.000 description 3
- BLJUARPJFKOELT-UHFFFAOYSA-N 4-propyl-n,n-bis(prop-2-ynyl)heptan-4-amine;hydrochloride Chemical compound Cl.CCCC(CCC)(CCC)N(CC#C)CC#C BLJUARPJFKOELT-UHFFFAOYSA-N 0.000 description 3
- LLMCTRDPUVISRI-UHFFFAOYSA-N 4-propyl-n-prop-2-ynylheptan-4-amine;hydrochloride Chemical compound Cl.CCCC(CCC)(CCC)NCC#C LLMCTRDPUVISRI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 208000018300 basal ganglia disease Diseases 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- LIQWRQIWHRKUEA-UHFFFAOYSA-N n-methyl-4-propylheptan-4-amine Chemical compound CCCC(CCC)(CCC)NC LIQWRQIWHRKUEA-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 208000009132 Catalepsy Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- UVJZHDXANGLWDQ-UHFFFAOYSA-N N,2-dimethyl-N-propylheptan-4-amine Chemical compound CN(C(CCC)CC(C)C)CCC UVJZHDXANGLWDQ-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 206010047853 Waxy flexibility Diseases 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- -1 aralkyl radical Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 230000002438 mitochondrial effect Effects 0.000 description 2
- SGXHFXAKUUHEIB-UHFFFAOYSA-N n,2-dimethyl-4-propylheptan-4-amine;hydrochloride Chemical compound Cl.CCCC(CCC)(CC(C)C)NC SGXHFXAKUUHEIB-UHFFFAOYSA-N 0.000 description 2
- LILGNMKYDJIDKZ-UHFFFAOYSA-N n,n,2-trimethyl-4-propylheptan-4-amine Chemical compound CCCC(CCC)(CC(C)C)N(C)C LILGNMKYDJIDKZ-UHFFFAOYSA-N 0.000 description 2
- YVIKUCATSFJPNF-UHFFFAOYSA-N n-methyl-4-propylheptan-4-amine;hydrochloride Chemical compound [Cl-].CCCC(CCC)(CCC)[NH2+]C YVIKUCATSFJPNF-UHFFFAOYSA-N 0.000 description 2
- UVBMZKBIZUWTLV-UHFFFAOYSA-N n-methyl-n-propylpropan-1-amine Chemical class CCCN(C)CCC UVBMZKBIZUWTLV-UHFFFAOYSA-N 0.000 description 2
- 230000002474 noradrenergic effect Effects 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- PEXCMMDHBIFUIJ-UHFFFAOYSA-N 2-[carbamimidoyl(methyl)amino]acetic acid;sulfuric acid Chemical compound OS(O)(=O)=O.NC(=N)N(C)CC(O)=O PEXCMMDHBIFUIJ-UHFFFAOYSA-N 0.000 description 1
- BURSRJBGGVCXTO-UHFFFAOYSA-N 2-methyl-N-prop-2-ynylheptan-4-amine Chemical compound C(C#C)NC(CCC)CC(C)C BURSRJBGGVCXTO-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VQIAWQKBOAUGHE-UHFFFAOYSA-N 4-propylheptan-4-amine Chemical compound CCCC(N)(CCC)CCC VQIAWQKBOAUGHE-UHFFFAOYSA-N 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N 7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione Chemical compound COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- NHPMEGBBKLLQDZ-UHFFFAOYSA-N C(C#C)NC(CCC)(C(C)C)CCC Chemical compound C(C#C)NC(CCC)(C(C)C)CCC NHPMEGBBKLLQDZ-UHFFFAOYSA-N 0.000 description 1
- VBORHMJJBNKVIW-UHFFFAOYSA-N CN(CC#C)C(CCC)(CC(C)C)CCC Chemical compound CN(CC#C)C(CCC)(CC(C)C)CCC VBORHMJJBNKVIW-UHFFFAOYSA-N 0.000 description 1
- JWJHKCOKBRKEND-UHFFFAOYSA-N CN(CC#C)C(CCC)(CCC)CCC Chemical compound CN(CC#C)C(CCC)(CCC)CCC JWJHKCOKBRKEND-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YKWIMNLMCMZIGE-UHFFFAOYSA-N Cl.C(C#C)NC(CCC)(CC(C)C)CCC Chemical compound Cl.C(C#C)NC(CCC)(CC(C)C)CCC YKWIMNLMCMZIGE-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000570065 Domene Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- UGRNFCNRNWAUFN-UHFFFAOYSA-N N,2-dimethyl-N-propylhexan-3-amine Chemical compound CN(C(CCC)C(C)C)CCC UGRNFCNRNWAUFN-UHFFFAOYSA-N 0.000 description 1
- MQVLPIBGNREZJA-UHFFFAOYSA-N N,N-dipropylheptan-3-amine Chemical compound C(CCC)C(CC)N(CCC)CCC MQVLPIBGNREZJA-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000003354 anti-apomorphinic effect Effects 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CLJMMQGDJNYDER-UHFFFAOYSA-N heptan-4-amine Chemical compound CCCC(N)CCC CLJMMQGDJNYDER-UHFFFAOYSA-N 0.000 description 1
- UNEPJNUFVDMRKA-UHFFFAOYSA-N heptan-4-amine;hydrochloride Chemical compound [Cl-].CCCC([NH3+])CCC UNEPJNUFVDMRKA-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 230000002698 inhibitory effect on catalepsy Effects 0.000 description 1
- 230000000195 inhibitory effect on catatonia Effects 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- ZIUTZNGAPLZTRC-UHFFFAOYSA-N n,2-dimethylheptan-4-amine Chemical compound CCCC(NC)CC(C)C ZIUTZNGAPLZTRC-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI823149A FI823149A7 (fi) | 1976-06-03 | 1977-06-03 | Menetelmä terapeuttisesti vaikuttavien di-n-propyylimetyyliamiinijohdannaisten valmistamiseksi. |
| FI823148A FI68219C (fi) | 1976-06-03 | 1982-09-10 | Foerfarande foer framstaellning av terapeutiskt aktiva di-n-propylmetylaminderivat |
| FI823147A FI68218C (fi) | 1976-06-03 | 1982-09-10 | Foerfarande foer framstaellning av terapeutiskt aktiva di-n-propylmetylaminderivat |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE842528 | 1976-06-03 | ||
| BE842528 | 1976-06-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI771780A7 FI771780A7 (enrdf_load_stackoverflow) | 1977-12-04 |
| FI63015B FI63015B (fi) | 1982-12-31 |
| FI63015C true FI63015C (fi) | 1983-04-11 |
Family
ID=3861370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI771780A FI63015C (fi) | 1976-06-03 | 1977-06-03 | Foerfarande foer framstaellning av terapeutiskt aktiva di-n-propylmetylaminderivat |
Country Status (17)
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES437790A1 (es) * | 1974-05-20 | 1977-05-16 | Labaz | Procedimiento para preparar composiciones farmaceuticas y veterinarias. |
| BE842528R (fr) * | 1976-06-03 | 1976-12-03 | Derives actifs de methylamine, compositions therapeutiques les contenant ainsi que les procedes de preparation de ces derives et compositions |
-
1977
- 1977-05-14 GR GR53468A patent/GR61148B/el unknown
- 1977-05-20 NZ NZ184161A patent/NZ184161A/xx unknown
- 1977-05-24 YU YU01295/77A patent/YU129577A/xx unknown
- 1977-05-25 ZA ZA00773151A patent/ZA773151B/xx unknown
- 1977-05-27 FR FR7716280A patent/FR2374901A1/fr active Granted
- 1977-05-27 AU AU25561/77A patent/AU511705B2/en not_active Ceased
- 1977-06-02 SE SE7706448A patent/SE452317B/xx not_active IP Right Cessation
- 1977-06-02 NO NO771941A patent/NO145337C/no unknown
- 1977-06-02 AR AR267925A patent/AR213646A1/es active
- 1977-06-02 DK DK244677A patent/DK146063C/da not_active IP Right Cessation
- 1977-06-02 PT PT66623A patent/PT66623B/pt unknown
- 1977-06-02 NL NL7706052A patent/NL7706052A/xx not_active Application Discontinuation
- 1977-06-03 ES ES459466A patent/ES459466A1/es not_active Expired
- 1977-06-03 JP JP52066217A patent/JPS6039261B2/ja not_active Expired
- 1977-06-03 FI FI771780A patent/FI63015C/fi not_active IP Right Cessation
- 1977-06-03 MX MX775778U patent/MX4778E/es unknown
- 1977-06-03 AT AT395877A patent/AT352088B/de not_active IP Right Cessation
-
1978
- 1978-03-21 FR FR7808094A patent/FR2372795A1/fr active Granted
- 1978-04-26 AR AR271897A patent/AR215053A1/es active
- 1978-04-26 AR AR271895A patent/AR215052A1/es active
- 1978-04-26 AR AR271896A patent/AR215175A1/es active
- 1978-05-31 ES ES470379A patent/ES470379A1/es not_active Expired
-
1982
- 1982-11-12 SE SE8206445A patent/SE452763B/sv not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: SANOFI |