CA1076482A - Produit therapeutique contenant des derives actifs de methylamine, et methode de preparation connexe - Google Patents

Produit therapeutique contenant des derives actifs de methylamine, et methode de preparation connexe

Info

Publication number: CA1076482A
Authority: CA; Canada
Prior art keywords: pharmaceutical; propyl; active ingredient; butylamine; veterinary composition
Prior art date: 1976-06-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA279,749A

Other languages

English (en)

Inventor

Charles Pigerol

Pierre Eymard

Madeleine Broll

Jean-Claude Vernieres

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Labaz SA

Original Assignee

Labaz SA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-06-03

Filing date

1977-06-02

Publication date

1980-04-29

1977-06-02 Application filed by Labaz SA filed Critical Labaz SA

1979-10-19 Priority to CA338,050A priority Critical patent/CA1078837A/fr

1980-04-29 Application granted granted Critical

1980-04-29 Publication of CA1076482A publication Critical patent/CA1076482A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 48
238000000034 method Methods 0.000 title description 9
230000001225 therapeutic effect Effects 0.000 title description 5
125000000250 methylamino group Chemical class [H]N(*)C([H])([H])[H] 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 67
239000002253 acid Substances 0.000 claims abstract description 22
239000004480 active ingredient Substances 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 11
125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
239000003937 drug carrier Substances 0.000 claims abstract description 7
208000018737 Parkinson disease Diseases 0.000 claims abstract description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000002431 hydrogen Chemical group 0.000 claims description 5
238000007911 parenteral administration Methods 0.000 claims description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 3
229920002472 Starch Polymers 0.000 claims description 3
229930006000 Sucrose Natural products 0.000 claims description 3
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
239000001768 carboxy methyl cellulose Substances 0.000 claims description 3
235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 3
239000008112 carboxymethyl-cellulose Substances 0.000 claims description 3
229940110456 cocoa butter Drugs 0.000 claims description 3
235000019868 cocoa butter Nutrition 0.000 claims description 3
235000013681 dietary sucrose Nutrition 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
235000019359 magnesium stearate Nutrition 0.000 claims description 3
235000019698 starch Nutrition 0.000 claims description 3
229960004793 sucrose Drugs 0.000 claims description 3
239000000454 talc Substances 0.000 claims description 3
229910052623 talc Inorganic materials 0.000 claims description 3
235000012222 talc Nutrition 0.000 claims description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
IOHZJCCMJGFCGF-UHFFFAOYSA-N n,n-dimethyl-4-propylheptan-4-amine Chemical compound CCCC(CCC)(CCC)N(C)C IOHZJCCMJGFCGF-UHFFFAOYSA-N 0.000 claims 1
RJWSUDHKAMWWDK-UHFFFAOYSA-N n-ethyl-4-propylheptan-4-amine Chemical compound CCCC(CCC)(CCC)NCC RJWSUDHKAMWWDK-UHFFFAOYSA-N 0.000 claims 1
UUTIEDHDKCISQX-UHFFFAOYSA-N n-ethyl-n-methyl-4-propylheptan-4-amine Chemical compound CCCC(CCC)(CCC)N(C)CC UUTIEDHDKCISQX-UHFFFAOYSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 15
229960003805 amantadine Drugs 0.000 description 15
-1 alkyl radical Chemical class 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
238000007792 addition Methods 0.000 description 11
238000002360 preparation method Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
206010007776 catatonia Diseases 0.000 description 9
239000013078 crystal Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 7
125000004433 nitrogen atom Chemical group N* 0.000 description 7
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
239000007788 liquid Substances 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
150000003956 methylamines Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 6
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 5
239000000725 suspension Substances 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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
206010044565 Tremor Diseases 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000003176 neuroleptic agent Substances 0.000 description 4
230000000701 neuroleptic effect Effects 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
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000000939 antiparkinson agent Substances 0.000 description 3
230000005587 bubbling Effects 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
230000003291 dopaminomimetic effect Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
230000000638 stimulation Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000000859 sublimation Methods 0.000 description 3
230000008022 sublimation Effects 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
208000009132 Catalepsy Diseases 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 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
150000008064 anhydrides Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000000295 complement effect Effects 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
230000002474 noradrenergic effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
238000009987 spinning Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
229940025084 amphetamine Drugs 0.000 description 1
230000003354 anti-apomorphinic effect Effects 0.000 description 1
239000012223 aqueous fraction Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
229940005991 chloric acid Drugs 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000095 emetic effect Effects 0.000 description 1
230000001037 epileptic effect Effects 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
201000003102 mental depression Diseases 0.000 description 1
230000003340 mental effect Effects 0.000 description 1
UFALMGBBEQMIQP-UHFFFAOYSA-N n,n,2-trimethyl-4-propylheptan-4-amine;hydrochloride Chemical compound [Cl-].CCCC(CCC)(CC(C)C)[NH+](C)C UFALMGBBEQMIQP-UHFFFAOYSA-N 0.000 description 1
CCRUHKGZAQXBKC-UHFFFAOYSA-N n-(2-methylpropyl)butan-1-amine Chemical compound CCCCNCC(C)C CCRUHKGZAQXBKC-UHFFFAOYSA-N 0.000 description 1
HFOVYKMFOFLDLN-UHFFFAOYSA-N n-propan-2-yl-4-propylheptan-4-amine Chemical compound CCCC(CCC)(CCC)NC(C)C HFOVYKMFOFLDLN-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000005303 weighing Methods 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA279,749A 1976-06-03 1977-06-02 Produit therapeutique contenant des derives actifs de methylamine, et methode de preparation connexe Expired CA1076482A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA338,050A CA1078837A (fr)	1976-06-03	1979-10-19	Derives actifs de methylamine, produits pharmaceutiques qui en derivent et procedes de preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
BE167579A BE842528R (fr)	1976-06-03	1976-06-03	Derives actifs de methylamine, compositions therapeutiques les contenant ainsi que les procedes de preparation de ces derives et compositions

Publications (1)

Publication Number	Publication Date
CA1076482A true CA1076482A (fr)	1980-04-29

Family

ID=3842891

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA279,749A Expired CA1076482A (fr)	1976-06-03	1977-06-02	Produit therapeutique contenant des derives actifs de methylamine, et methode de preparation connexe

Country Status (9)

Country	Link
BE (1)	BE842528R (fr)
CA (1)	CA1076482A (fr)
CH (4)	CH624922A5 (fr)
DE (1)	DE2725245C2 (fr)
GB (3)	GB1565021A (fr)
HU (1)	HU175776B (fr)
IE (1)	IE45730B1 (fr)
IT (1)	IT1114869B (fr)
OA (1)	OA05675A (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GR61148B (en) *	1976-06-03	1978-09-27	Labaz	Preparation process of active methylamine derivatives
DE3362734D1 (en) *	1982-01-18	1986-05-07	Exxon Research Engineering Co	Secondary and tertiary amino alcohols
DE19827161A1 (de) *	1998-06-18	1999-12-23	Merck Patent Gmbh	Verfahren zur katalytischen, symmetrischen Disubstitution von Carbonsäureamiden mit Grignardreagenzien
EP1087929A1 (fr) *	1998-06-18	2001-04-04	MERCK PATENT GmbH	Procede pour preparer des bibliotheques combinatoires d'amines
DE19827166A1 (de) *	1998-06-18	1999-12-23	Merck Patent Gmbh	Verfahren zur katalytischen Disubstitution von Carbonsäureamiden mit wenigstens einem Grignardreagenz

1976
- 1976-06-03 BE BE167579A patent/BE842528R/fr not_active IP Right Cessation
1977
- 1977-05-27 CH CH660677A patent/CH624922A5/fr not_active IP Right Cessation
- 1977-05-30 GB GB22842/77A patent/GB1565021A/en not_active Expired
- 1977-05-30 GB GB18083/78A patent/GB1565022A/en not_active Expired
- 1977-05-30 GB GB46520/78A patent/GB1565023A/en not_active Expired
- 1977-05-31 IT IT24186/77A patent/IT1114869B/it active
- 1977-06-01 IE IE1131/77A patent/IE45730B1/en unknown
- 1977-06-02 CA CA279,749A patent/CA1076482A/fr not_active Expired
- 1977-06-02 HU HU77LA917A patent/HU175776B/hu unknown
- 1977-06-03 DE DE2725245A patent/DE2725245C2/de not_active Expired
- 1977-06-03 OA OA56184A patent/OA05675A/fr unknown
1980
- 1980-09-17 CH CH698080A patent/CH623559A5/fr not_active IP Right Cessation
- 1980-09-17 CH CH697980A patent/CH623560A5/fr not_active IP Right Cessation
- 1980-09-17 CH CH697880A patent/CH624389A5/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE2725245C2 (de)	1986-09-04
CH624389A5 (en)	1981-07-31
IE45730L (en)	1977-12-03
CH624922A5 (en)	1981-08-31
GB1565022A (en)	1980-04-16
GB1565023A (en)	1980-04-16
CH623559A5 (en)	1981-06-15
IE45730B1 (en)	1982-11-17
DE2725245A1 (de)	1977-12-15
BE842528R (fr)	1976-12-03
OA05675A (fr)	1981-05-31
IT1114869B (it)	1986-01-27
CH623560A5 (en)	1981-06-15
GB1565021A (en)	1980-04-16
HU175776B (hu)	1980-10-28

Legal Events

Date	Code	Title	Description
1997-04-29	MKEX	Expiry

Publication	Publication Date	Title
JPS6089474A (ja)	1985-05-20	モルフイナン誘導体，その製造方法，及び該化合物を含有する抗腫瘍剤
FR2460919A1 (fr)	1981-01-30	Amino-ethers oxydes, leur procede de preparation et leur application en therapeutique
IE42409B1 (en)	1980-07-30	Acetylene derivatives of amino acids
CA1076482A (fr)	1980-04-29	Produit therapeutique contenant des derives actifs de methylamine, et methode de preparation connexe
US4151303A (en)	1979-04-24	Phenoxyalkylcarboxylic acid compounds and serum-lipid and triglyceride depressing therapeutic compositions
CH655100A5 (fr)	1986-03-27	1-cyclohexenyl-2-(hydroxy- ou chloro-)ethyl-pyrrolidine et procede pour sa preparation.
EP0077427B1 (fr)	1985-05-22	Dérivés de pipéridine, leur procédé de préparation et leur application en thérapeutique
HK1000541B (en)	1998-04-03	Benzene derivates, their preparation and pharmaceutical compositions containing them
US4622430A (en)	1986-11-11	Derivatives of pentacyclo undecanes, processes for preparing these compounds, and pharmaceutical compositions thereof
US4201725A (en)	1980-05-06	Secondary amines
EP0106776B1 (fr)	1986-10-22	Nouvelles amino-2 aminométhyl-5 oxazolines-2
US2880209A (en)	1959-03-31	Piperazine quaternary salts having parasitical activity and method of making
US3066167A (en)	1962-11-27	4-amino-3, 5-dichloro-benzamides
EP0187509A2 (fr)	1986-07-16	9-Aminoalkylfluorènes
US3213140A (en)	1965-10-19	2-phenyl-4, 6-dichlorophenoxyethylamine and salts thereof
CH637112A5 (fr)	1983-07-15	Derives benzylideniques.
US4026925A (en)	1977-05-31	Active derivatives of methylamine, therapeutic compositions containing the same and processes for preparing the said derivatives and compositions
US4511566A (en)	1985-04-16	2-N-Cycloalkylmethyl 3-oxo 5,6-diaryl-as-triazines
CA1078837A (fr)	1980-06-03	Derives actifs de methylamine, produits pharmaceutiques qui en derivent et procedes de preparation
US4057644A (en)	1977-11-08	Active derivatives of methylamine in therapeutic compositions and methods of use
US3973025A (en)	1976-08-03	1,4-Dihydro-3,5-pyridine dicarbonitrile derivatives
US3133959A (en)	1964-05-19	Haloalkyl-1, 3-propanediol dicarbamates
IE45731B1 (en)	1982-11-17	Methylamine derivatives and process for preparing the same
GB2077258A (en)	1981-12-16	Alkoxy-acyl carnitines process for their preparation and pharmaceutical compositions containing same
GB2178035A (en)	1987-02-04	Novel benzamides and their preparation and therapeutic application