KR840001167A - 티아졸리딘알킬렌 피페라진 유도체의 제조방법 - Google Patents
티아졸리딘알킬렌 피페라진 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840001167A KR840001167A KR1019820003482A KR820003482A KR840001167A KR 840001167 A KR840001167 A KR 840001167A KR 1019820003482 A KR1019820003482 A KR 1019820003482A KR 820003482 A KR820003482 A KR 820003482A KR 840001167 A KR840001167 A KR 840001167A
- Authority
- KR
- South Korea
- Prior art keywords
- pyrimidinyl
- pharmaceutically useful
- thiazolidinedione
- piperazinyl
- butyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000004885 piperazines Chemical class 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- 239000002253 acid Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- -1 alkali metal salt Chemical class 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 239000012458 free base Substances 0.000 claims 3
- NURSVPNIOIFOQH-UHFFFAOYSA-N 3-(4-bromobutyl)-1,3-thiazolidine-2,4-dione Chemical compound BrCCCCN1C(=O)CSC1=O NURSVPNIOIFOQH-UHFFFAOYSA-N 0.000 claims 2
- GEOSQGJVNAMYLC-UHFFFAOYSA-N 3-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 GEOSQGJVNAMYLC-UHFFFAOYSA-N 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 1
- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 claims 1
- 229940123464 Thiazolidinedione Drugs 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- AFNJMVYFZNHDRX-UHFFFAOYSA-N [C]1=NC=CC=N1 Chemical class [C]1=NC=CC=N1 AFNJMVYFZNHDRX-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000008238 pharmaceutical water Substances 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/34—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Description
Claims (4)
- 하기 구조식(Ⅱ)의 티아졸리디온과 하기 구조식(Ⅲ)의 피페라진을, 충분한 시간동안 약 50℃ 내지 200℃의 온도에서 염기 존재하에 또는 않이, 불활성 반응매체에서 반응시키는, 하기 구조식(Ⅰ)의 화합물의 제조방법.R1은 저급알킬 또는 수소, n은 2내지 5의 정수, Z는인 R2치환된 페닐라디칼, R2는 수소, 할로겐, 저급알킬, 저급알콕시 또는 트리플루오로메틸, n은 3,4 또는 5Z는 2-피리미디닐 또는인 R3치환된 2-피리미디닐라디칼, R3은 수소, 시아노 또는 그로 인한 약학적인 수용성 비독성상 부가염, A는 독자적으로 수소, 알칼리 금속염 또는 X-(CH2)n-라디칼인데, X는 반응성 에스테르기의 산 잔여기 n은 2내지 5의 정수, 및/또한 만일 필요하다면 구조식(Ⅰ)의 생성된 화합물은 유리화합물 또는 그외의 염으로 전환될 수 있는 염으로 전환된다.
- 제1항에 있어서, 충분한 시간동안 불활성 용매의 환류 상태에서 염기의 존재하에 3-(4-브로모부틸-2,4-티아졸리딘디온과 1-(2-피리미디닐)피페라진을 반응시 켜 3-[4-[4-(2-피리미디닐)-1-피페라지닐]-부틸]-2,4-티아졸리딘디온의 유리된 염기를 생성한후, 상기 유리된 염기를 약학적으로 유용한 산과 약학적으로 유용한 산부가염으로 전환시키는 것으로 이루어진 3-[4-[4-(2-피리미디닐)-1-피페라지닐]-부틸]-2,4-티아졸리딘디온과 그의 약학적으로 유용한 산부가염의 제조방법.
- 제1항에 있어서, 충분한 시간동안 불활성용매의 환류상태에서, 염기의 존재하에 3-(4-브로모부틸)-2,4-티아졸리딘 디온과 1-(3|트리플루오로메틸페닐)-피페라진을 반응시켜 3-[4-[4-[3-(트리플루오로메틸)-페닐]-1-피페라지닐]-부틸]-2,4-티아졸리딘의 유리염기를 생성한뒤 상기 유리된 염기를 약학적으로 유용한산과 약학적으로 유용한 산부가염으로 전환시키는 것으로 이루어진 3-[4-[4-[3-(트리플루오로메틸)-페닐]-1-피페라지닐]-부틸]-2,40티아졸리딘디온과 그의 학적으로 유용한 산부가염의 제조방법.
- 실시예 1,2,3과 4-14에 서술된 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US289352 | 1981-08-03 | ||
US06/289,352 US4367335A (en) | 1981-08-03 | 1981-08-03 | Thiazolidinylalkylene piperazine derivatives |
US289.352 | 1981-08-03 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840001167A true KR840001167A (ko) | 1984-03-28 |
KR880001478B1 KR880001478B1 (ko) | 1988-08-13 |
Family
ID=23111164
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR8203482A KR880001478B1 (ko) | 1981-08-03 | 1982-08-03 | 티아졸리디닐 알킬렌 피페라진 유도체의 제조방법 |
Country Status (28)
Country | Link |
---|---|
US (1) | US4367335A (ko) |
JP (2) | JPS5826877A (ko) |
KR (1) | KR880001478B1 (ko) |
AT (1) | AT381705B (ko) |
AU (1) | AU560655B2 (ko) |
BE (1) | BE894022A (ko) |
CA (1) | CA1172636A (ko) |
CH (1) | CH652398A5 (ko) |
DE (1) | DE3228990A1 (ko) |
DK (1) | DK162991C (ko) |
ES (1) | ES8307800A1 (ko) |
FI (1) | FI76793C (ko) |
FR (1) | FR2510572B1 (ko) |
GB (1) | GB2106104B (ko) |
GR (1) | GR76172B (ko) |
HU (1) | HU191187B (ko) |
IE (1) | IE53641B1 (ko) |
IL (1) | IL66434A0 (ko) |
IT (1) | IT1149329B (ko) |
LU (1) | LU84316A1 (ko) |
NL (1) | NL8203034A (ko) |
NZ (1) | NZ201159A (ko) |
OA (1) | OA07172A (ko) |
PH (1) | PH18220A (ko) |
PT (1) | PT75366B (ko) |
SE (1) | SE452320B (ko) |
YU (1) | YU44074B (ko) |
ZA (1) | ZA825479B (ko) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4456756A (en) * | 1981-08-03 | 1984-06-26 | Mead Johnson & Company | Spirothiazolidinyl piperazine derivatives |
US4452799A (en) * | 1981-12-23 | 1984-06-05 | Mead Johnson & Company | Benzisothiazole and benzisoxazole piperazine derivatives |
US4620006A (en) * | 1982-08-11 | 1986-10-28 | Eastman Kodak Company | Acid salts of 1-(cyanoalkyl)-4-guanylpiperazines |
US4619930A (en) * | 1985-01-16 | 1986-10-28 | Bristol-Myers Company | Antipsychotic cyclic imide derivatives of 2-(4-butylpiperazin-1-yl)pyridines, compositions and use |
CA1278792C (en) * | 1985-05-06 | 1991-01-08 | Joseph P. Yevich | Antipsychotic fused-ring pyridinylpiperazine derivatives |
US4677104A (en) * | 1985-05-06 | 1987-06-30 | Bristol-Myers Company | Antipsychotic fused-ring pyridinylpiperazine derivatives |
US4675403A (en) * | 1985-10-16 | 1987-06-23 | American Home Products Corporation | 3-Aminoalkyl derivatives of 5,5-disubstituted hydantoins with psychotropic activity |
US4784998A (en) * | 1987-04-06 | 1988-11-15 | Bristol-Myers Company | 1,3,4-oxadiazole pyschotropic compounds |
US5801186A (en) * | 1987-11-20 | 1998-09-01 | Hoechst Marion Roussel, Inc. | 3- 4-(1-substituted-4-piperazinyl)butyl!-4-thiazolidinone and related compounds |
US4880930A (en) * | 1987-11-30 | 1989-11-14 | New James S | Psychotropic acyclic amide derivatives |
US5001130A (en) * | 1988-02-18 | 1991-03-19 | Bristol-Myers Company | Psychotropic heterobicycloalkylpiperazine derivatives |
US5116970A (en) * | 1988-02-18 | 1992-05-26 | New James S | Psychotropic heterobicycloalkylpiperazine derivatives: 2. fused pyridazinones |
US4780466A (en) * | 1988-03-17 | 1988-10-25 | Hoechst-Roussel Pharmaceuticals, Inc. | Arylpiperazinylalkoxy derivatives of cyclic imides |
FR2642759B1 (fr) * | 1989-02-09 | 1991-05-17 | Laboratorios Esteve Sa | Derives de pyrimidyl-piperazinyl-alkyl azoles avec activite anxiolytique et/ou tranquillisante |
JPH0415948U (ko) * | 1990-05-31 | 1992-02-10 | ||
US5194436A (en) * | 1991-01-10 | 1993-03-16 | Hoechst-Roussel Pharmaceuticals Inc. | 1-piperazinyl-2-butenes and -2-butynes |
US5130315A (en) * | 1991-01-10 | 1992-07-14 | Raymond R. Wittekind | 1-piperazinyl-2-butenes and -2-butynes |
US20040077605A1 (en) * | 2001-06-20 | 2004-04-22 | Salvati Mark E. | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
WO2003093236A1 (en) * | 2002-05-02 | 2003-11-13 | Euro-Celtique, S.A. | 1-(pyrid-2-yl)-piperazine compounds as metabotropic glutamate receptor inhibitor |
WO2006013445A2 (en) * | 2004-07-28 | 2006-02-09 | Ranbaxy Laboratories Limited | Thiazolidinedione derivatives as alpha adrenergic receptor antagonists |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2672460A (en) * | 1952-06-24 | 1954-03-16 | American Cyanamid Co | Disubstituted piperazines and methods of preparing the same |
US2748125A (en) * | 1954-04-26 | 1956-05-29 | American Cyanamid Co | 1-substituted-4-sulfamylpiperazine and method of preparing the same |
NL125835C (ko) * | 1960-05-24 | |||
FR1435004A (fr) * | 1965-02-04 | 1966-04-15 | Sobio Lab | Dérivés de thiazolidine-dione-2, 4- et procédé de préparation |
US3398151A (en) * | 1966-02-01 | 1968-08-20 | Mead Johnson & Co | Azaspirodecanediones and azaspiroundecanediones |
DE1695410A1 (de) * | 1967-04-20 | 1971-04-08 | Merck Patent Gmbh | Verfahren zur Herstellung von 1-(Thiazolyl-5-alkyl)-4-(pyridyl-2)-piperazinen |
US3635976A (en) * | 1967-12-20 | 1972-01-18 | Pennwalt Corp | 1 - heterocyclic alkyl-1 2 3 4-tetrahydroquinazolinones and analgesic intermediates thereof |
US3822266A (en) * | 1968-12-24 | 1974-07-02 | Hoffmann La Roche | (3-(1-piperazinyl)-2-hydroxy-propoxy)acetanilides |
BE759371A (fr) * | 1969-11-24 | 1971-05-24 | Bristol Myers Co | Azaspirodecanediones heterocycliques et procedes pour leur preparation |
IT1052119B (it) * | 1972-10-16 | 1981-06-20 | Sigma Tau Ind Farmaceuti | Derivati del triazolinone e procedimento per la loro preparazione |
US3976776A (en) * | 1972-12-06 | 1976-08-24 | Mead Johnson & Company | Tranquilizer process employing N-(heteroarcyclic)piperazinylalkylazaspiroalkanediones |
US4017622A (en) * | 1972-12-18 | 1977-04-12 | Dainippon Pharmaceutical Co., Ltd. | Piperazine derivatives |
DE2263211A1 (de) * | 1972-12-23 | 1974-07-04 | Boehringer Sohn Ingelheim | Neue arylpiperazine und verfahren zu ihrer herstellung |
US3919230A (en) * | 1974-02-07 | 1975-11-11 | Smithkline Corp | {62 -Naphthylmethyl piperazinyl derivatives |
FR2285883A1 (fr) * | 1974-09-30 | 1976-04-23 | Cerm Cent Europ Rech Mauvernay | Nouveaux composes chimiques a activite bronchospasmolytique et antitussive, et procede pour leur obtention |
US3940398A (en) * | 1975-01-23 | 1976-02-24 | E. R. Squibb & Sons, Inc. | 2-[[4-(Azine or diazine or triazine)-1-piperazinyl]alkyl]-1H-benz[de]isoquinoline-1,3(2H)-diones |
US4026894A (en) * | 1975-10-14 | 1977-05-31 | Abbott Laboratories | Antihypertensive agents |
US4060615A (en) * | 1976-02-18 | 1977-11-29 | Mead Johnson & Company | 2-Piperazinyl-6,7-dimethoxyquinazolines |
US4001237A (en) * | 1976-02-18 | 1977-01-04 | Bristol-Myers Company | Oxazole, isoxazole, thiazole and isothiazole amides |
GB1518559A (en) * | 1976-04-12 | 1978-07-19 | Science Union & Cie | Naphthyl derivatives processes for their preparation an pharmaceutical compositions containing them |
US4078063A (en) * | 1976-09-24 | 1978-03-07 | Merck & Co., Inc. | Piperazinylpyridines |
US4101548A (en) * | 1977-02-22 | 1978-07-18 | Bristol-Myers Company | 1,2,3-Thiadiazole amides |
HU173380B (hu) * | 1977-02-25 | 1979-04-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novogo proizvodnogo piridil-piperazina i kislo-additivnykh solejj |
DE2727469A1 (de) * | 1977-06-18 | 1978-12-21 | Hoechst Ag | Neue hexahydropyrimidine, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
US4138561A (en) * | 1977-09-30 | 1979-02-06 | Bristol-Myers Company | Cyanocarboxamidines and quinazoline process |
EP0002978B1 (fr) * | 1977-12-29 | 1982-10-06 | Synthelabo | Dérivés de thiazolidinedione-2,4, leur préparation et leur application en thérapeutique |
FR2418798A1 (fr) * | 1978-03-03 | 1979-09-28 | Science Union & Cie | Nouvelles piperazines disubstituees, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
US4182763A (en) * | 1978-05-22 | 1980-01-08 | Mead Johnson & Company | Buspirone anti-anxiety method |
IL57569A0 (en) * | 1978-06-20 | 1979-10-31 | Synthelabo | Phenylpiperazine derivative,their preparation and pharmaceutical compositions containing them |
US4161595A (en) * | 1978-10-02 | 1979-07-17 | Bristol-Myers Company | Levulinic acid salt |
-
1981
- 1981-08-03 US US06/289,352 patent/US4367335A/en not_active Expired - Fee Related
-
1982
- 1982-07-05 NZ NZ201159A patent/NZ201159A/en unknown
- 1982-07-06 AU AU85663/82A patent/AU560655B2/en not_active Ceased
- 1982-07-13 GR GR68741A patent/GR76172B/el unknown
- 1982-07-20 YU YU1586/82A patent/YU44074B/xx unknown
- 1982-07-23 ES ES514264A patent/ES8307800A1/es not_active Expired
- 1982-07-28 FR FR8213177A patent/FR2510572B1/fr not_active Expired
- 1982-07-29 NL NL8203034A patent/NL8203034A/nl not_active Application Discontinuation
- 1982-07-29 IT IT48909/82A patent/IT1149329B/it active
- 1982-07-29 ZA ZA825479A patent/ZA825479B/xx unknown
- 1982-07-30 DK DK343682A patent/DK162991C/da active
- 1982-07-30 FI FI822667A patent/FI76793C/fi not_active IP Right Cessation
- 1982-07-30 PH PH27654A patent/PH18220A/en unknown
- 1982-07-30 CA CA000408450A patent/CA1172636A/en not_active Expired
- 1982-07-30 IE IE1852/82A patent/IE53641B1/en not_active IP Right Cessation
- 1982-08-01 IL IL66434A patent/IL66434A0/xx not_active IP Right Cessation
- 1982-08-02 GB GB08222212A patent/GB2106104B/en not_active Expired
- 1982-08-02 HU HU822485A patent/HU191187B/hu not_active IP Right Cessation
- 1982-08-02 SE SE8204550A patent/SE452320B/sv not_active IP Right Cessation
- 1982-08-02 CH CH4661/82A patent/CH652398A5/de not_active IP Right Cessation
- 1982-08-02 PT PT75366A patent/PT75366B/pt not_active IP Right Cessation
- 1982-08-03 DE DE19823228990 patent/DE3228990A1/de not_active Withdrawn
- 1982-08-03 BE BE0/208748A patent/BE894022A/fr not_active IP Right Cessation
- 1982-08-03 OA OA57765A patent/OA07172A/xx unknown
- 1982-08-03 KR KR8203482A patent/KR880001478B1/ko active
- 1982-08-03 AT AT0299482A patent/AT381705B/de not_active IP Right Cessation
- 1982-08-03 JP JP57134808A patent/JPS5826877A/ja active Granted
- 1982-08-03 LU LU84316A patent/LU84316A1/fr unknown
-
1990
- 1990-03-29 JP JP2079032A patent/JPH02270821A/ja active Granted
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