FI65424C - Foerfarande foer framstaellning av terapeutiskt verksamma derivat av naftalen-aettiksyra - Google Patents

Foerfarande foer framstaellning av terapeutiskt verksamma derivat av naftalen-aettiksyra Download PDF

Info

Publication number: FI65424C
Authority: FI; Finland
Prior art keywords: cyclohexyl; acid; aettikyyra; verksamma; naftalen
Prior art date: 1977-10-03

Application number

FI782993A

Other languages

English (en)

Finnish (fi)

Other versions

FI782993A7 (fi

FI65424B (fi

Inventor

Jean-Jacques Godfroid

Efroim Steiner

Original Assignee

Cerm Cent Europ Rech Mauvernay

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.)

1977-10-03

Filing date

1978-10-02

Publication date

1984-05-10

1978-10-02 Application filed by Cerm Cent Europ Rech Mauvernay filed Critical Cerm Cent Europ Rech Mauvernay

1979-04-04 Publication of FI782993A7 publication Critical patent/FI782993A7/fi

1984-01-31 Publication of FI65424B publication Critical patent/FI65424B/fi

1984-05-10 Application granted granted Critical

1984-05-10 Publication of FI65424C publication Critical patent/FI65424C/fi

Links

150000001875 compounds Chemical class 0.000 claims description 20
238000000034 method Methods 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 10
-1 4-cyclohexyl Chemical group 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical class C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 claims description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
239000012346 acetyl chloride Substances 0.000 claims description 3
230000020477 pH reduction Effects 0.000 claims description 3
150000001351 alkyl iodides Chemical class 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
238000007127 saponification reaction Methods 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
239000005971 1-naphthylacetic acid Substances 0.000 claims 1
IIDAJRNSZSFFCB-UHFFFAOYSA-N 4-amino-5-methoxy-2-methylbenzenesulfonamide Chemical compound COC1=CC(S(N)(=O)=O)=C(C)C=C1N IIDAJRNSZSFFCB-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
BPXITDRZRADOHD-UHFFFAOYSA-N 2-(4-cyclohexylnaphthalen-1-yl)acetic acid Chemical compound C12=CC=CC=C2C(CC(=O)O)=CC=C1C1CCCCC1 BPXITDRZRADOHD-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
229960002895 phenylbutazone Drugs 0.000 description 4
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
230000002757 inflammatory effect Effects 0.000 description 3
IODOJATXTVKMEB-UHFFFAOYSA-N methyl 2-(4-cyclohexylnaphthalen-1-yl)propanoate Chemical compound C12=CC=CC=C2C(C(C)C(=O)OC)=CC=C1C1CCCCC1 IODOJATXTVKMEB-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
VZUGVMQFWFVFBX-UHFFFAOYSA-N 2-(4-cyclohexyl-1-naphthyl)propanoic acid Chemical compound C12=CC=CC=C2C(C(C(O)=O)C)=CC=C1C1CCCCC1 VZUGVMQFWFVFBX-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YCBGZXAJACCOAD-UHFFFAOYSA-N 1-(chloromethyl)-4-cyclohexylnaphthalene Chemical compound C12=CC=CC=C2C(CCl)=CC=C1C1CCCCC1 YCBGZXAJACCOAD-UHFFFAOYSA-N 0.000 description 1
RAYZALBEMJMGEA-UHFFFAOYSA-N 1-cyclohexylnaphthalene Chemical compound C1CCCCC1C1=CC=CC2=CC=CC=C12 RAYZALBEMJMGEA-UHFFFAOYSA-N 0.000 description 1
101100275770 Caenorhabditis elegans cri-3 gene Proteins 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000011324 bead Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000009826 neoplastic cell growth Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000009291 secondary effect Effects 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
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 1
230000001225 therapeutic effect Effects 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pain & Pain Management (AREA)
Rheumatology (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)

FI782993A 1977-10-03 1978-10-02 Foerfarande foer framstaellning av terapeutiskt verksamma derivat av naftalen-aettiksyra FI65424C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7729728		1977-10-03
FR7729728A FR2404620A2 (fr)	1977-10-03	1977-10-03	Derives de l'acide cyclohexyl-4 naphtalene acetique-1, procede d'obtention et application a titre de medicament

Publications (3)

Publication Number	Publication Date
FI782993A7 FI782993A7 (fi)	1979-04-04
FI65424B FI65424B (fi)	1984-01-31
FI65424C true FI65424C (fi)	1984-05-10

Family

ID=9196050

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI782993A FI65424C (fi)	1977-10-03	1978-10-02	Foerfarande foer framstaellning av terapeutiskt verksamma derivat av naftalen-aettiksyra

Country Status (17)

Country	Link
US (1)	US4218473A (ja)
JP (1)	JPS5461161A (ja)
AT (1)	AT356089B (ja)
AU (1)	AU521195B2 (ja)
BE (1)	BE870553A (ja)
CA (1)	CA1100527A (ja)
CH (1)	CH635307A5 (ja)
DE (1)	DE2842495C2 (ja)
DK (1)	DK150846C (ja)
ES (1)	ES473909A1 (ja)
FI (1)	FI65424C (ja)
FR (1)	FR2404620A2 (ja)
GB (1)	GB2006763B (ja)
GR (1)	GR66032B (ja)
NL (2)	NL185143C (ja)
PT (1)	PT68611A (ja)
SE (1)	SE442993B (ja)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103183604B (zh) *	2011-12-28	2015-07-29	药源药物化学（上海）有限公司	维达洛芬的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3904682A (en) *	1967-01-13	1975-09-09	Syntex Corp	2-(6{40 -Methoxy-2{40 -naphthyl)acetic acid
US3896157A (en) *	1967-01-13	1975-07-22	Syntex Corp	Dihydo 2-naphthylacetic acid derivatives
FR2115026B1 (ja) *	1970-11-24	1974-03-22	Logeais Labor Jacques

1977
- 1977-10-03 FR FR7729728A patent/FR2404620A2/fr active Granted
1978
- 1978-09-18 BE BE190544A patent/BE870553A/xx not_active IP Right Cessation
- 1978-09-26 US US05/945,891 patent/US4218473A/en not_active Expired - Lifetime
- 1978-09-28 AU AU40266/78A patent/AU521195B2/en not_active Expired
- 1978-09-29 DE DE2842495A patent/DE2842495C2/de not_active Expired
- 1978-09-29 GR GR57337A patent/GR66032B/el unknown
- 1978-09-29 DK DK432478A patent/DK150846C/da not_active IP Right Cessation
- 1978-10-02 FI FI782993A patent/FI65424C/fi not_active IP Right Cessation
- 1978-10-02 CA CA312,498A patent/CA1100527A/fr not_active Expired
- 1978-10-02 CH CH1021378A patent/CH635307A5/fr not_active IP Right Cessation
- 1978-10-02 JP JP12142378A patent/JPS5461161A/ja active Granted
- 1978-10-02 SE SE7810294A patent/SE442993B/sv not_active IP Right Cessation
- 1978-10-02 NL NLAANVRAGE7809949,A patent/NL185143C/xx not_active IP Right Cessation
- 1978-10-02 PT PT68611A patent/PT68611A/pt unknown
- 1978-10-03 GB GB7839192A patent/GB2006763B/en not_active Expired
- 1978-10-03 ES ES473909A patent/ES473909A1/es not_active Expired
- 1978-10-03 AT AT713578A patent/AT356089B/de not_active IP Right Cessation
1996
- 1996-03-05 NL NL960003C patent/NL960003I2/nl unknown

Also Published As

Publication number	Publication date
DE2842495C2 (de)	1983-05-19
NL185143C (nl)	1990-02-01
JPS5640140B2 (ja)	1981-09-18
DK432478A (da)	1979-04-04
GR66032B (ja)	1981-01-14
DK150846C (da)	1988-02-01
FR2404620A2 (fr)	1979-04-27
AT356089B (de)	1980-04-10
FR2404620B2 (ja)	1980-08-01
NL185143B (nl)	1989-09-01
US4218473A (en)	1980-08-19
FI782993A7 (fi)	1979-04-04
AU521195B2 (en)	1982-03-18
SE7810294L (sv)	1979-04-04
NL7809949A (nl)	1979-04-05
PT68611A (fr)	1978-11-01
BE870553A (fr)	1979-03-19
ES473909A1 (es)	1979-04-01
ATA713578A (de)	1979-09-15
DE2842495A1 (de)	1979-04-19
CH635307A5 (fr)	1983-03-31
GB2006763B (en)	1982-03-17
GB2006763A (en)	1979-05-10
NL960003I1 (nl)	1996-05-01
CA1100527A (fr)	1981-05-05
JPS5461161A (en)	1979-05-17
DK150846B (da)	1987-07-06
NL960003I2 (nl)	1996-11-01
FI65424B (fi)	1984-01-31
AU4026678A (en)	1980-04-03
SE442993B (sv)	1986-02-10

Publication	Publication Date	Title
JP2919030B2 (ja)	1999-07-12	キノン誘導体
US3780061A (en)	1973-12-18	Tricyclic ketonic compounds
US3763229A (en)	1973-10-02	Indan-1-carboxylic acid derivatives
FI65424C (fi)	1984-05-10	Foerfarande foer framstaellning av terapeutiskt verksamma derivat av naftalen-aettiksyra
US4337353A (en)	1982-06-29	Novel carboxylic acids, benzoyl phenyl alkanoic acids and use thereof
US3803235A (en)	1974-04-09	Novel acetophenone oxime derivatives
US4362891A (en)	1982-12-07	Alkanoic acid derivatives
US3919316A (en)	1975-11-11	2-Aminodichlorotetralins
US4515946A (en)	1985-05-07	6,11-Dihydro-11-oxo-dibenz-[b,e]oxepin derivatives
NO131930B (ja)	1975-05-20
US4461912A (en)	1984-07-24	Phenylacetic acid derivatives, their preparation and compositions containing them
US4116972A (en)	1978-09-26	Anti-inflammatory 1-oxo-isoindoline derivatives and processes for their preparation
JPS584699B2 (ja)	1983-01-27	置換フエニル酢酸誘導体及びその製法
CS216206B2 (en)	1982-10-29	Method of making the derivatives of the diphenylpyrazole
US3876683A (en)	1975-04-08	(n-carboxymethyl)biphenyl acetamides
CH640818A5 (fr)	1984-01-31	Derives d'acide naphtyl-1 acetique, leurs procedes de preparation et medicament les contenant.
KR830000654B1 (ko)	1983-03-25	테트라하이드로-2H-벤조[c]피롤의 제조방법
US4166125A (en)	1979-08-28	2-oxo-phenylbutanoic acid derivatives
US4051260A (en)	1977-09-27	2-Substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes, and derivatives thereof, and methods and compositions for the use thereof
GB2027022A (en)	1980-02-13	Pyridoxine derivatives and their use
US3975540A (en)	1976-08-17	2-Substituted-5-oxo-5H-dibenzo(a,d)cycloheptenes, and derivatives thereof, and methods and compositions for the use thereof
US3919309A (en)	1975-11-11	Acyl substituted phenyl alkanoic acids
Gh et al.	1987	Synthesis of tritium‐labelled 2‐(3′‐carboxypropyl)‐3‐imino‐6 para‐methoxy phenyl‐2, 3‐dihydropyridazine ([3H] SR95531)
LU86706A1 (fr)	1987-07-24	Nouveaux derives du benzo(4,5)cyclohepta(1,2-b)thiophene,leur preparation et leur utilisation comme medicaments
KR850001036B1 (ko)	1985-07-19	2-아미노-4-메틸피리딘의 아미드의 제조방법

Legal Events

Date	Code	Title	Description
1978-10-02	MA	Patent expired
2004-08-31	MA	Patent expired	Owner name: CENTRE EUROPéEN DE RECHERCHES MAUVERNEY