KR840000568A - 두고리 피리미딘-5-온 유도체의 제조방법 - Google Patents
두고리 피리미딘-5-온 유도체의 제조방법 Download PDFInfo
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- KR840000568A KR840000568A KR1019820002847A KR820002847A KR840000568A KR 840000568 A KR840000568 A KR 840000568A KR 1019820002847 A KR1019820002847 A KR 1019820002847A KR 820002847 A KR820002847 A KR 820002847A KR 840000568 A KR840000568 A KR 840000568A
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- Prior art keywords
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- general formula
- compound
- acid addition
- lower alkyl
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- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical class O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 title claims 4
- 238000000034 method Methods 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims 16
- 239000002253 acid Substances 0.000 claims 12
- 239000003814 drug Substances 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- 239000012442 inert solvent Substances 0.000 claims 4
- -1 4-fluorobenzoyl Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- KAIRZPVWWIMPFT-UHFFFAOYSA-N 3-piperidin-4-yl-1h-indole Chemical compound C1CNCCC1C1=CNC2=CC=CC=C12 KAIRZPVWWIMPFT-UHFFFAOYSA-N 0.000 claims 1
- MGWXSWNURQSQHA-UHFFFAOYSA-N 6-(2-chloroethyl)-3,7-dimethyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CC1=C(CCCl)C(=O)N2C(C)=CSC2=N1 MGWXSWNURQSQHA-UHFFFAOYSA-N 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- GRHBQAYDJPGGLF-UHFFFAOYSA-N isothiocyanic acid Chemical compound N=C=S GRHBQAYDJPGGLF-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 claims 1
- 230000000506 psychotropic effect Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- 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)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (52)
1) W가 적당한 이탈기인 일반식 :
의 적당한 반응 에스테르를 일반식 :
의 적당히 치환된 피페리딘과 적당한 반응성 불활성 용매에서 반응시키거나 ; 또는
2) 일반식 :
또는
의 중간체를 L이 적당한 이탈기인 일반식 :
와
의 고리화제와 적당한 반응 불활성 용매에서 각각 반응시키거나, 또는
3) 일반식 :
의 2-메트캅로피를미디는을 W'가 적당한 이탈기인 일반식 :
또는
의 시약과 적합한 반응 미 불활성 용매에서 반응시키거나, 또는
4) 일반식 :
의 시약을 구조식
의 이소티오시안산업과 적당한 반응 불활성 용매에서 반응시키는데, Q가 일반식 (a)의 기인 경우에는, 임의로 이갈이 하여 얻은 일반식 :
의 화합물을, 일반식 :
또는
의 화합물로 적당한 하이드록실에 대한 카르보닐 환원 매질과 적당한 메틸렌에 대한 카르보닐 환원매질에서 각각 전환시키거나 또는 임의로 (I-d)에서 카르보닐 기능을 케탈화하거나 또는 임의로 일반식 (I-c)의 화합물을 일반식 :
의 화합물에 (I-c)를 적당한 저급 알칸산과 할로겐화산 또는 산무수물과 반응시키고 임의로 전환시키고, 또 Q가 일반식 (b)의 기인 경우에는 이같이 하여 얻은 일반식 :
의 화합물을 일반식 :
의 화합물로 (I-b)를 적합한 산화매질에서 반응시키고 또 계속해서 이같이 하여 생성된 아미드 :
를 가수분해하여서 전환시켜서 일반식
을 제조하고 이를 적당한 산으로 처리하여 약제로서 유용한 비독성 산부가염으로 전환시키거나 또는 반대로 산부가임을 알카리로 염기화하고 또 이 물질의 입체화학적 이성체를 제조하는 방법(이 식에서, R1은 수소, 저급알킬 또는 Ar; R2는 수소, 저급알킬 또는 Ar; R3는 수소 또는 저급알킬 ; Alk는 저급 알칸디일기이고, A는 구조식 -CH1-CH2-, -CH2-CH2-CH2-,혹은을 가지며 유황원자에 부착된 탄소원자를 갖는 2가기로서 여기에 R4, R5와 R6는 각기 독립적으로 수소와 저급 알킬로 구성된 그룹으로부터 선택되고 또한 R4, R5는 5 혹은 6개의 포화 또는 불포화 카르복실산 환으로 환성될 수 있고 선택적으로 저급 알킬기로서 치환될 수 있는 것이고, Q는 구조식 -X-Ar (a)을 갖는 기로서 구성된 그룹으로 부터 선택된 일원으로서, 여기에서 X는 (O 저급 알킬)2,와으로 구성된 그룹으로부터 선택된 구성요소인데, 상기 R7은 수소나 저급 알킬이며, q는 정수 2 혹은 3인 것과, 또 일반식,
을 갖는 기로서 여기에서 R8은 수소나 저급 알킬이고 R9, R10및 R11은 수소나 할로겐으로 구성된 그룹으로 부터 각기 독립적으로 선택된 기로부터 선택된 일원이며, Ar은 페닐 혹은 치환페닐로서 치환 페닐은 아미노그룹과 혹은 1, 2나 3개의 할로겐원자를 가진다.)
청구의 범위 1에서 제조된 일반식 (Ⅰ)의 화합물.
6-(2-클로로에틸)-3,7-디메틸-5H-티아졸로[3,2-a]피리미딘-5-온을3-(4-피페리디닐)-1H-인돌과 반응시키는 것과 또한 원한다면 이것의 약제로 사용할 수 있는 산부가염을 제조하는 것을 특징으로 한 6-[2-[4-(1H-인돌-3-일)-1-피페리딘일]에틸]-3,7-디메틸-5H-티아졸로[3,2-a] 피디미딘-5-온과 이것의 약제로 사용할 수 있는 산부가염으로 된 기로부터 선택되는 화합물을 제조하는 방법.
청구의 범위 3에서 제조된 화합물.
6-(2-클로로에틸(-2,3-디히드로-7-메틸-5H-디아졸로[3,2-a] 피리미딘-5-온을(4-플루오로페닐)-(4-피페리딘일) 메탄온과 반응시키는 것과 또한, 만일 필요하다면 이것의 약제로 사용할 수 있는 산부가염을 제조함을 특징으로 한 6-[2-[4-(4-플루오로벤조일)-1-피페리딘] 에틸]-2,3-디히드로-7-메틸-5H-티아졸로[3,2-a]피티미딘-5-온과 이것의 약제로 사용할 수 있는 산부가염으로 된 기로부터 선택되는 화합물을 제조하는 방법.
청구의 범위 5에서 제조된 화합물.
6-(2-클로로에틸)-3,7-디메틸-5H-티아졸로[3,2-a]피리미딘-5-온을 (4-플루오로페닐) (4-피페리딘일)-메탄온과 반응시키는 것과 또한 필요하다면, 이것의 약제로 사용할 수 있는 산부가염을 제조하는 것을 특징으로 한 6-[2-[4-(4-플루오로벤조일)-1-피페리딘일]에틸]-3,7-디메틸-5H-티아졸로[3,2-a]피리미딘-5-온과 이것의 약제로 사용할 수 있는 산부가염으로 된 기로부터 선택되는 화합물을 제조하는 방법.
청구의 범위 7에서 제조된 화합물.
불활성 담체와 유효성분을 갖고 상기 청구의 범위 1의 일반식 (Ⅰ)인 화합물의 약제로서의 유효량이 2개의 환을 갖는 피리미딘-5-온 유도체 및 약제로 사용 가능한 이 물질의 산부가염과 또 이 물질의 입체화학적 이성질체들로 구성된 그룹으로 부터 선택된 화합물을 함유한 정신흥분질병을 치료하는 약제 조성물의 제조방법.
상기 청구의 범위 1의 물질의 두 개의 환을 갖는 피리미딘-5-온 유도체와 이 물질의 약제로 사용 가능한 산부가염 및 이 물질의 엽체화적 이성체로 구성된 그룹으로부터 선택된 화합물을 약제 유효량 투여하여 정신흡분병 온혈동물을 치료하는 방법.
※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28359081A | 1981-07-15 | 1981-07-15 | |
| US283590 | 1981-07-15 | ||
| US370653 | 1982-04-21 | ||
| US06/370,653 US4443451A (en) | 1981-07-15 | 1982-04-21 | Bicyclic pyrimidin-5-one derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840000568A true KR840000568A (ko) | 1984-02-25 |
| KR870000868B1 KR870000868B1 (ko) | 1987-04-30 |
Family
ID=26962133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8202847A KR870000868B1 (ko) | 1981-03-15 | 1982-06-25 | 두고리 피리미딘-5-온 유도체의 제조방법 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4443451A (ko) |
| EP (1) | EP0070053B1 (ko) |
| KR (1) | KR870000868B1 (ko) |
| AU (1) | AU547967B2 (ko) |
| CA (1) | CA1207765A (ko) |
| CS (1) | CS227690B2 (ko) |
| DD (1) | DD215553A5 (ko) |
| DE (1) | DE3270589D1 (ko) |
| DK (1) | DK160314C (ko) |
| ES (1) | ES8308327A1 (ko) |
| FI (1) | FI75828C (ko) |
| GR (1) | GR76006B (ko) |
| HU (1) | HU186952B (ko) |
| IE (1) | IE53400B1 (ko) |
| MA (1) | MA19536A1 (ko) |
| NO (1) | NO166327C (ko) |
| NZ (1) | NZ201266A (ko) |
| PH (1) | PH18120A (ko) |
| PL (1) | PL136680B1 (ko) |
| PT (1) | PT75247B (ko) |
| SU (1) | SU1138032A3 (ko) |
| YU (1) | YU154682A (ko) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4535081A (en) * | 1979-11-23 | 1985-08-13 | Pfizer Inc. | Antiallergic and antiulcer 1-oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides and intermediates therefor |
| US4548938A (en) * | 1981-07-15 | 1985-10-22 | Janssen Pharmaceutica N.V. | 5-H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one compounds |
| US4485107A (en) * | 1982-11-01 | 1984-11-27 | Janssen Pharmaceutica N.V. | [[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones |
| GB8300728D0 (en) * | 1983-01-12 | 1983-02-16 | Erba Farmitalia | Substituted carboxy-thiazolo / 3 2 - a / pyrimidine derivatives |
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| IL90879A0 (en) * | 1988-09-02 | 1990-02-09 | Janssen Pharmaceutica Nv | 3-piperidinyl-indazole derivatives,their preparation and antihypertensive compositions containing them |
| US5140029A (en) * | 1989-01-09 | 1992-08-18 | Janssen Pharmaceutica N.V. | 2-aminopyrimidinone derivatives |
| US5256659A (en) * | 1989-01-09 | 1993-10-26 | Janssen Pharmaceutica N.V. | 2-aminopyrimidinone derivatives |
| GB8900382D0 (en) * | 1989-01-09 | 1989-03-08 | Janssen Pharmaceutica Nv | 2-aminopyrimidinone derivatives |
| FR2644786B1 (fr) * | 1989-03-21 | 1993-12-31 | Adir Cie | Nouveaux derives fluoro-4 benzoiques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| WO1992006086A1 (en) * | 1990-10-01 | 1992-04-16 | Janssen Pharmaceutica N.V. | Novel 4-piperidinylcarbonyl derivatives |
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| ATE445838T1 (de) | 2001-07-25 | 2009-10-15 | Raptor Pharmaceutical Inc | Zusammensetzungen und verfahren zur modulation des transports durch die blut-hirn-schranke |
| EP1615923A1 (en) * | 2003-04-22 | 2006-01-18 | Synthon B.V. | Risperidone monohydrochloride |
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| ES2401129T3 (es) * | 2006-12-19 | 2013-04-17 | F. Hoffmann-La Roche Ag | Derivados de heteroaril-pirrolidinil- y -piperidinil-cetona |
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| HUE059078T2 (hu) | 2009-02-20 | 2022-10-28 | Enhanx Biopharm Inc | Glutation-alapú hatóanyagszállító rendszer |
| JP2012526144A (ja) | 2009-05-06 | 2012-10-25 | ラボラトリー スキン ケア インコーポレイテッド | 活性物質−リン酸カルシウム粒子複合体を含む経皮送達組成物およびその使用方法 |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1306558A (en) * | 1970-08-14 | 1973-02-14 | Seperic | Derivatives of thiazolino-pyrimidin-5-ones their preparation and applications |
| GB1374281A (en) * | 1971-08-24 | 1974-11-20 | Seperic | Thiazolino-pyrimidin-5-one derivatives process for their pre paration and applications thereof |
| JPS51146497A (en) * | 1975-06-12 | 1976-12-16 | Sankyo Co Ltd | Process for preparing pyrido (1,2-a)pyrimidinone derivatives |
| US4041163A (en) * | 1976-03-29 | 1977-08-09 | Pfizer Inc. | N-(5-Tetrazolyl)-4-oxo-4H-pyrimido(2,1-b)benzothiazole-3-carboxamide antiallergy agents |
| GB1582744A (en) * | 1976-06-04 | 1981-01-14 | Gruenenthal Gmbh | 7h-thiazolo (and 1,3,4-thiadiazolo-)(3,2-a) pyrimidin-7-one-5-carboxylic acids derivatives and medicaments therof |
| US4471117A (en) * | 1979-06-21 | 1984-09-11 | Janssen Pharmaceutica N.V. | 3,4-Dihydro-2H-pyrimido(2,1-b)benzothiazoles |
| US4342870A (en) * | 1980-03-28 | 1982-08-03 | Janssen Pharmaceutica N.V. | Novel 3-(1-piperidinylalkyl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives |
-
1982
- 1982-04-21 US US06/370,653 patent/US4443451A/en not_active Expired - Fee Related
- 1982-05-28 CA CA000403953A patent/CA1207765A/en not_active Expired
- 1982-06-02 CS CS824092A patent/CS227690B2/cs unknown
- 1982-06-17 DE DE8282200751T patent/DE3270589D1/de not_active Expired
- 1982-06-17 EP EP82200751A patent/EP0070053B1/en not_active Expired
- 1982-06-23 GR GR68542A patent/GR76006B/el unknown
- 1982-06-24 SU SU823455997A patent/SU1138032A3/ru active
- 1982-06-25 KR KR8202847A patent/KR870000868B1/ko active
- 1982-07-09 AU AU85759/82A patent/AU547967B2/en not_active Ceased
- 1982-07-14 DK DK316582A patent/DK160314C/da not_active IP Right Cessation
- 1982-07-14 NO NO822439A patent/NO166327C/no unknown
- 1982-07-14 IE IE1689/82A patent/IE53400B1/en not_active IP Right Cessation
- 1982-07-14 FI FI822511A patent/FI75828C/fi not_active IP Right Cessation
- 1982-07-14 NZ NZ201266A patent/NZ201266A/en unknown
- 1982-07-14 MA MA19744A patent/MA19536A1/fr unknown
- 1982-07-14 ES ES513976A patent/ES8308327A1/es not_active Expired
- 1982-07-14 PT PT75247A patent/PT75247B/pt not_active IP Right Cessation
- 1982-07-15 DD DD82241675A patent/DD215553A5/de not_active IP Right Cessation
- 1982-07-15 HU HU822299A patent/HU186952B/hu not_active IP Right Cessation
- 1982-07-15 PH PH27576A patent/PH18120A/en unknown
- 1982-07-15 PL PL1982237492A patent/PL136680B1/pl unknown
- 1982-07-15 YU YU01546/82A patent/YU154682A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR76006B (ko) | 1984-08-03 |
| PH18120A (en) | 1985-03-22 |
| EP0070053A2 (en) | 1983-01-19 |
| FI75828B (fi) | 1988-04-29 |
| YU154682A (en) | 1985-03-20 |
| KR870000868B1 (ko) | 1987-04-30 |
| DE3270589D1 (de) | 1986-05-22 |
| HU186952B (en) | 1985-10-28 |
| EP0070053A3 (en) | 1984-03-21 |
| FI822511A0 (fi) | 1982-07-14 |
| IE821689L (en) | 1983-01-15 |
| NO822439L (no) | 1983-01-17 |
| DK316582A (da) | 1983-01-16 |
| DK160314C (da) | 1991-07-29 |
| NO166327C (no) | 1991-07-10 |
| ES513976A0 (es) | 1983-08-16 |
| NO166327B (no) | 1991-03-25 |
| NZ201266A (en) | 1985-01-31 |
| SU1138032A3 (ru) | 1985-01-30 |
| CA1207765A (en) | 1986-07-15 |
| IE53400B1 (en) | 1988-11-09 |
| DD215553A5 (de) | 1984-11-14 |
| FI822511L (fi) | 1983-01-16 |
| AU8575982A (en) | 1983-01-20 |
| AU547967B2 (en) | 1985-11-14 |
| MA19536A1 (fr) | 1983-04-01 |
| ES8308327A1 (es) | 1983-08-16 |
| PT75247A (en) | 1982-08-01 |
| PL136680B1 (en) | 1986-03-31 |
| US4443451A (en) | 1984-04-17 |
| PT75247B (en) | 1985-01-07 |
| PL237492A1 (en) | 1984-02-27 |
| EP0070053B1 (en) | 1986-04-16 |
| FI75828C (fi) | 1988-08-08 |
| DK160314B (da) | 1991-02-25 |
| CS227690B2 (en) | 1984-05-14 |
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