FI62667C - Foerfarande foer framstaellning av antiemetiska 1-(benzazolylalkyl)piperidinderivat - Google Patents
Foerfarande foer framstaellning av antiemetiska 1-(benzazolylalkyl)piperidinderivat Download PDFInfo
- Publication number
- FI62667C FI62667C FI762086A FI762086A FI62667C FI 62667 C FI62667 C FI 62667C FI 762086 A FI762086 A FI 762086A FI 762086 A FI762086 A FI 762086A FI 62667 C FI62667 C FI 62667C
- Authority
- FI
- Finland
- Prior art keywords
- dihydro
- benzimidazol
- parts
- formula
- piperidinyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 230000003474 anti-emetic effect Effects 0.000 claims description 13
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- MKZOYCWVYJRSAQ-UHFFFAOYSA-N 1-(3-chloropropyl)-3-prop-1-en-2-ylbenzimidazol-2-one Chemical compound C1=CC=C2N(CCCCl)C(=O)N(C(=C)C)C2=C1 MKZOYCWVYJRSAQ-UHFFFAOYSA-N 0.000 description 4
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- 241000282472 Canis lupus familiaris Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 238000007126 N-alkylation reaction Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000003354 anti-apomorphinic effect Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000002006 anti-spasmogenic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000008641 benzimidazolones Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- RMEDXOLNCUSCGS-UHFFFAOYSA-N droperidol Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CC=C(N2C(NC3=CC=CC=C32)=O)CC1 RMEDXOLNCUSCGS-UHFFFAOYSA-N 0.000 description 1
- 229960000394 droperidol Drugs 0.000 description 1
- 239000002895 emetic Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 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
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- VKUFWEJGPRFEOH-UHFFFAOYSA-N imidazol-2-one hydrate Chemical compound O.O=C1N=CC=N1 VKUFWEJGPRFEOH-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000004694 iodide salts 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
- 239000012948 isocyanate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XRSHTORJYMIIHI-UHFFFAOYSA-N n-(4-chloro-2-nitrophenyl)piperidin-4-amine;hydrobromide Chemical compound Br.[O-][N+](=O)C1=CC(Cl)=CC=C1NC1CCNCC1 XRSHTORJYMIIHI-UHFFFAOYSA-N 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
- 229950001675 spiperone Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Otolaryngology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI813935A FI65249C (fi) | 1975-07-21 | 1981-12-08 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-enyl-8-bensimidazol-1-ylpropyl-1,3,8-triazaspiro(4,5)deka n--onderivat |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59779375A | 1975-07-21 | 1975-07-21 | |
| US59779375 | 1975-07-21 | ||
| US05/687,139 US4066772A (en) | 1975-07-21 | 1976-05-17 | 1,3-Dihydro-1-[3-(1-piperidinyl)propyl]-2H-benzimidazol-2-ones and related compounds |
| US68713976 | 1976-05-17 | ||
| KR760001697 | 1976-07-12 | ||
| KR7601697A KR810000334B1 (ko) | 1975-07-21 | 1976-07-12 | 1-(벤즈 아조릴알킬) 피페리딘 유도체의 제조방법 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI762086A7 FI762086A7 (enrdf_load_stackoverflow) | 1977-01-22 |
| FI62667B FI62667B (fi) | 1982-10-29 |
| FI62667C true FI62667C (fi) | 1983-02-10 |
Family
ID=27348142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI762086A FI62667C (fi) | 1975-07-21 | 1976-07-20 | Foerfarande foer framstaellning av antiemetiska 1-(benzazolylalkyl)piperidinderivat |
Country Status (25)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501749A (en) * | 1983-10-31 | 1985-02-26 | Merck & Co., Inc. | Peripherally selective dopamine antagonists in the treatment of ocular hypertension |
| JPS6248684A (ja) * | 1985-08-26 | 1987-03-03 | Sumitomo Chem Co Ltd | 新規なヨ−ドブチロフエノン誘導体およびその製造法 |
| JPS62251313A (ja) * | 1986-04-25 | 1987-11-02 | 信越ポリマー株式会社 | 結束装置 |
| US6355659B1 (en) | 1994-07-29 | 2002-03-12 | Laboratorios Del Dr. Esteve, S.A. | 4-(4-Chlorophenyl)-1236-tetrahydro-1(1H-124-triazol-1-yl)butty)pyrideine and salts thereof; pharmaceutical compositions and method of treating psychoses utilizing same |
| FR2723091B1 (fr) * | 1994-07-29 | 1996-11-08 | Esteve Labor Dr | Tetrahydropyridine-(6,4-hydroxypiperidine) alkylazoles |
| RU2192848C1 (ru) * | 2001-10-30 | 2002-11-20 | Закрытое акционерное общество "ВЕРОФАРМ" | Противорвотное средство |
| PA8603801A1 (es) * | 2003-05-27 | 2004-12-16 | Janssen Pharmaceutica Nv | Derivados de la quinazolina |
| RU2268047C2 (ru) * | 2003-12-15 | 2006-01-20 | Закрытое акционерное общество "Фармацевтическое предприятие "Оболенское" | Лекарственная форма, обладающая противорвотным действием, и способ ее изготовления |
| MXPA06007017A (es) | 2003-12-18 | 2006-08-31 | Janssen Pharmaceutica Nv | Derivados de pirido y pirimidopirimidina como agentes antiproliferativos. |
| NI200700147A (es) | 2004-12-08 | 2019-05-10 | Janssen Pharmaceutica Nv | Derivados de quinazolina inhibidores de cinasas dirigidos a multip |
| DK2044084T3 (en) | 2006-07-13 | 2016-05-09 | Janssen Pharmaceutica Nv | MTKI-quinazoline derivatives |
| EP1997805A1 (en) * | 2007-06-01 | 2008-12-03 | Commissariat à l'Energie Atomique | Compounds with antiparasitic activity, applications thereof to the treatment of infectious diseases caused by apicomplexans |
| ES2562218T3 (es) | 2007-07-27 | 2016-03-03 | Janssen Pharmaceutica, N.V. | Pirrolopirimidinas útiles para el tratamiento de enfermedades proliferativas |
| KR20120102172A (ko) | 2007-08-31 | 2012-09-17 | 시오노기세이야쿠가부시키가이샤 | 치환-퀴녹살린-형 피페리딘 화합물 및 그의 용도 |
| US9090618B2 (en) | 2012-12-27 | 2015-07-28 | Purdue Pharma L.P. | Substituted benzimidazole-type piperidine compounds and uses thereof |
| US11364226B2 (en) | 2017-06-30 | 2022-06-21 | Cinrx Pharma, Llc | Deuterated domperidone compositions, methods, and preparation |
| WO2017136617A1 (en) * | 2016-02-04 | 2017-08-10 | Cinrx Pharma, Llc | Deuterated domperidone compositions and methods for therapy of disorders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE633495A (enrdf_load_stackoverflow) * | 1962-06-13 | |||
| BE633914A (enrdf_load_stackoverflow) * | 1962-06-22 | |||
| US3629267A (en) * | 1968-10-28 | 1971-12-21 | Smith Kline French Lab | Benzoheterocyclicalkyl derivatives of 4-(2-keto -1-benzimidazolinyl)-piperidine 4-(2-keto - 1 - benzimidazolinyl) -1 2 3 6 tetrahydropyridine 1 - phenyl - 1 3 8-triazaspiro(4 5)decan - 4 - one and 2 4 9-triazaspiro(5 5)undecan-1 3 5-trione |
| AU4698672A (en) * | 1972-09-22 | 1972-11-09 | Ciba-Geigy Ag | Azacycloaliphatic compounds, process for their manufacture and compositions containing them |
| FR2218100A1 (en) * | 1973-02-20 | 1974-09-13 | Janssen Pharmaceutica Nv | Neuroleptic tricyclic derivs. - of benzimidazolinones and triazaspiro-4,5-decan-4-ones |
| US3989707A (en) * | 1974-06-21 | 1976-11-02 | Janssen Pharmaceutica N.V. | Benzimidazolinone derivatives |
-
1976
- 1976-06-23 NZ NZ181256A patent/NZ181256A/xx unknown
- 1976-06-30 GB GB7627242A patent/GB1542514A/en not_active Expired
- 1976-07-07 CA CA256,450A patent/CA1085852A/en not_active Expired
- 1976-07-07 RO RO7686860A patent/RO70566A/ro unknown
- 1976-07-08 PH PH18663A patent/PH13710A/en unknown
- 1976-07-09 ES ES449740A patent/ES449740A1/es not_active Expired
- 1976-07-09 LU LU75354A patent/LU75354A1/xx unknown
- 1976-07-16 AU AU15964/76A patent/AU511027B2/en not_active Expired
- 1976-07-16 CS CS764688A patent/CS202550B2/cs unknown
- 1976-07-19 JP JP51085216A patent/JPS5217475A/ja active Granted
- 1976-07-19 IT IT50499/76A patent/IT1062614B/it active
- 1976-07-20 DK DK327576A patent/DK154950C/da not_active IP Right Cessation
- 1976-07-20 NL NLAANVRAGE7608023,A patent/NL187442C/xx not_active IP Right Cessation
- 1976-07-20 FI FI762086A patent/FI62667C/fi not_active IP Right Cessation
- 1976-07-20 AT AT0534776A patent/AT364358B/de not_active IP Right Cessation
- 1976-07-20 BG BG033791A patent/BG26526A3/xx unknown
- 1976-07-20 PT PT65387A patent/PT65387B/pt unknown
- 1976-07-20 IE IE1602/76A patent/IE43496B1/en not_active IP Right Cessation
- 1976-07-20 SE SE7608265A patent/SE426490B/xx not_active IP Right Cessation
- 1976-07-20 CH CH929176A patent/CH623820A5/de not_active IP Right Cessation
- 1976-07-21 DE DE19762632870 patent/DE2632870A1/de active Granted
- 1976-07-21 YU YU1794/76A patent/YU39969B/xx unknown
-
1977
- 1977-08-16 ES ES461630A patent/ES461630A1/es not_active Expired
- 1977-08-16 ES ES461631A patent/ES461631A1/es not_active Expired
-
1980
- 1980-03-20 HK HK141/80A patent/HK14180A/xx unknown
- 1980-12-11 SE SE8008713A patent/SE435621B/sv not_active IP Right Cessation
-
1981
- 1981-12-30 MY MY17/81A patent/MY8100017A/xx unknown
-
1982
- 1982-05-21 KE KE3215A patent/KE3215A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired | ||
| MA | Patent expired |
Owner name: JANSSEN PHARMACEUTICA N.V. |