KR850004959A - 아릴옥시-n-(아미노알킬)-1-피롤리딘 및 피페리딘 카복스 아미드 및 카보티오 아미드의 제조방법 - Google Patents
아릴옥시-n-(아미노알킬)-1-피롤리딘 및 피페리딘 카복스 아미드 및 카보티오 아미드의 제조방법 Download PDFInfo
- Publication number
- KR850004959A KR850004959A KR1019840002526A KR840002526A KR850004959A KR 850004959 A KR850004959 A KR 850004959A KR 1019840002526 A KR1019840002526 A KR 1019840002526A KR 840002526 A KR840002526 A KR 840002526A KR 850004959 A KR850004959 A KR 850004959A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- hydrogen
- carbon atoms
- reacted
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001408 amides Chemical class 0.000 title 1
- 125000004103 aminoalkyl group Chemical group 0.000 title 1
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 title 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- -1 2,3-dihydro-1H-inden-4-yl Chemical group 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 239000003440 toxic substance Substances 0.000 claims 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 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
- 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
- C07D211/40—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/12—Oxygen or sulfur atoms
-
- 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
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (1)
- 일반식(Ⅱ)의 화합물을 일반식(Ⅱ)의 화합물과 반응시키거나, 일반식(Ⅳ)의 화합물을 일반식(Ⅴ)의 화합물과 반응시키거나, X가 S이고 R이 수소인 화화물을 수득하기 위해서 일반식(Ⅵ)의 화합물을 일반식(Ⅶ)의 아미노 이스티오시아네이트와 반응시키거나, R1및 R2가 모두 수소인 화합물을 수득하기 위해서 일반식(Ⅷ)의 화합물을 히드라진과 반응시키거나, R1이 수소이고, R2가 메틸 라디칼인 화합물을 수득하기 위해서 R1및 R2가 모두 수소인 일반식(Ⅰ)의 화합물을 트리에틸오르토포르메이트와 반응시키고 이어서 수소화붕소나트륨과 반응시키거나, R1이 수소이고, R2가 저급알킬인 화합물을 수득하기 위해서 일반식(Ⅸ)의 화합물을 일반식(Ⅹ)의 화합물과 반응시킨후 가수분해시키고, 필요시 수득된 일반식(Ⅰ)의 화합물을 약제학적으로 무독한 염으로 전환시킴을 특징으로 하여, 일반식(Ⅰ)의 화합물 및 이의 약제학적으로 무독한 산부가염을 제조하는 방법.상기식에서, Ar은 1-나프틸, 2-나프틸, 2,3-디하이드로-1H-인덴-4-일, 2,3-디하이드로-1H-인덴-5-일, 페닐 또는 치환된 페닐(치환제는 탄소수 1 내지 8의 저급알킬, 탄소수 1 내지 8의 저급알콕시, 할로겐 및 트리플루오로메틸중에서 선택된다)이고, m 및 n은 1 또는 2이나, 동시에 2일 수는 없고, p는 1,2,3 또는 4이고, R은 수소 또는 탄소수 1 내지 3의 저급알킬이고, R1및 R2는 수소, 탄소수 1 내지 8의 저급알킬, 페닐, 탄소수 7 내지 9의 페닐저급알킬 또는 탄소수 3 내지 8의 시클로알킬이거나, R1및 R2는 인접원자와 결합하여 4-몰폴리노, 1-피롤리디노, 1-피페리디노, 1-피페라지노 및 4-저급알킬피페라진-1-일중에서 선택된 헤테로시클릭 잔기를 형성할 수 있고, X는 산소 또는 황이고, 단, 일반식(Ⅲ)에서 R이 수소가 아닐 경우 R1및 R2도 수소가 아니어야 하거나, R이 R1과 동일하고 R2는 수소이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US557,885? | 1983-12-05 | ||
| US06/557,885 US4547514A (en) | 1983-12-05 | 1983-12-05 | Aryloxy-N-(aminoalkyl)-1-pyrrolidine and piperidine carboxamides and carbothioamides having antiarrhythmic activity |
| US557,885 | 1983-12-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850004959A true KR850004959A (ko) | 1985-08-19 |
| KR900005133B1 KR900005133B1 (ko) | 1990-07-20 |
Family
ID=24227270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840002526A KR900005133B1 (ko) | 1983-12-05 | 1984-05-10 | 아릴옥시-n-(아미노알킬)-1-피롤리딘 및 피페리딘 카복스아미드 및 카보티오아미드의 제조방법, 및 이를 함유하는 약제조성물 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4547514A (ko) |
| EP (1) | EP0147909B1 (ko) |
| JP (1) | JPS60123466A (ko) |
| KR (1) | KR900005133B1 (ko) |
| AT (1) | ATE48413T1 (ko) |
| AU (1) | AU572747B2 (ko) |
| CA (1) | CA1227797A (ko) |
| DE (1) | DE3480651D1 (ko) |
| DK (1) | DK52784A (ko) |
| ES (4) | ES8601876A1 (ko) |
| HU (1) | HU193719B (ko) |
| IL (1) | IL70823A (ko) |
| PH (1) | PH20831A (ko) |
| PT (1) | PT78090B (ko) |
| ZA (1) | ZA84697B (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4812451A (en) * | 1984-10-19 | 1989-03-14 | A. H. Robins Company, Incorporated | 1-(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl)-α,.alpha. |
| US4810703A (en) * | 1984-10-19 | 1989-03-07 | A. H. Robins Company, Incorporated | 1-((aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl)-alpha, alpha-diarylpyrrolidine, piperidine and homopiperidineacetamides and acetonitriles |
| US4812452A (en) * | 1984-10-19 | 1989-03-14 | A. H. Robins Company, Incorporated | 1-((aminoalkyl and aminoalkylamino) carbonyl and thiocarbonyl)-α,α-diarylpyrrolidine, piperidine and homopiperidineacetamides and acetonitriles |
| US5183902A (en) * | 1985-02-28 | 1993-02-02 | A. H. Robins Company, Incorporated | Method of treating muscular tension, muscle spasticity and anxiety with 3-aryloxy and 3-arylthioazetidinecarboxamides |
| US5151418A (en) * | 1985-02-28 | 1992-09-29 | A. H. Robins Company, Incorporated | Method of treating muscular tension, muscle spasticity and anxiety with 3-aryloxy and 3-arylthioazetidinecarboxamides |
| DE3800868A1 (de) * | 1988-01-14 | 1989-07-27 | Thomae Gmbh Dr K | Mittel zur behandlung von bradycardien und bradyarrhythmien |
| US5212184A (en) * | 1988-03-14 | 1993-05-18 | Hoechst-Roussel Pharmaceuticals Inc. | 1-substituted-4-pentafluorophenoxypiperidines |
| US5192776A (en) * | 1988-03-14 | 1993-03-09 | Hoechst-Roussel Pharmaceuticals Incorporated | 1-subsituted-4-pentafluorophenoxypiperidines |
| WO2009051244A1 (ja) * | 2007-10-18 | 2009-04-23 | Takeda Pharmaceutical Company Limited | 複素環化合物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2831862A (en) * | 1956-02-27 | 1958-04-22 | Lakeside Lab Inc | Ethers of n-alkyl-3-hydroxypiperidine and salts thereof |
| US3577432A (en) * | 1968-12-23 | 1971-05-04 | Robins Co Inc A H | 1-substituted-3-phenoxypyrrolidines |
| US3577415A (en) * | 1968-12-23 | 1971-05-04 | Robins Co Inc A H | 1-substituted-3-substituted phenoxypyrrolidines |
| FR2315274A1 (fr) * | 1975-06-27 | 1977-01-21 | Parcor | Nouveaux derives de la thieno (2,3-c) pyridine, leur preparation et leurs applications |
| US4036957A (en) * | 1975-11-18 | 1977-07-19 | A. H. Robins Company, Inc. | Phenoxy compounds in combinations to suppress gastric bleeding in aspirin therapy |
| MX6634E (es) * | 1979-01-09 | 1985-09-12 | Robins Co Inc A H | Procedimiento para preparar el isomero trans de 3-ariloxi-4-hidroxipirrolidinas |
-
1983
- 1983-12-05 US US06/557,885 patent/US4547514A/en not_active Expired - Fee Related
-
1984
- 1984-01-30 IL IL70823A patent/IL70823A/xx unknown
- 1984-01-30 ZA ZA84697A patent/ZA84697B/xx unknown
- 1984-02-01 ES ES529364A patent/ES8601876A1/es not_active Expired
- 1984-02-01 AU AU23976/84A patent/AU572747B2/en not_active Ceased
- 1984-02-06 DK DK52784A patent/DK52784A/da not_active Application Discontinuation
- 1984-02-09 PH PH30213A patent/PH20831A/en unknown
- 1984-02-10 PT PT78090A patent/PT78090B/pt not_active IP Right Cessation
- 1984-03-23 JP JP59055975A patent/JPS60123466A/ja active Pending
- 1984-05-10 KR KR1019840002526A patent/KR900005133B1/ko active IP Right Grant
- 1984-06-13 AT AT84303995T patent/ATE48413T1/de not_active IP Right Cessation
- 1984-06-13 EP EP84303995A patent/EP0147909B1/en not_active Expired
- 1984-06-13 DE DE8484303995T patent/DE3480651D1/de not_active Expired - Fee Related
- 1984-06-18 CA CA000456806A patent/CA1227797A/en not_active Expired
- 1984-12-04 HU HU844476A patent/HU193719B/hu not_active IP Right Cessation
-
1985
- 1985-06-14 ES ES544169A patent/ES8802021A1/es not_active Expired
-
1986
- 1986-06-02 ES ES555591A patent/ES8802572A1/es not_active Expired
- 1986-06-02 ES ES555590A patent/ES8802571A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES555590A0 (es) | 1987-07-01 |
| ES529364A0 (es) | 1985-11-16 |
| ES555591A0 (es) | 1987-07-01 |
| IL70823A0 (en) | 1984-04-30 |
| CA1227797A (en) | 1987-10-06 |
| PH20831A (en) | 1987-04-30 |
| ES8802571A1 (es) | 1987-07-01 |
| DK52784D0 (da) | 1984-02-06 |
| ES8601876A1 (es) | 1985-11-16 |
| EP0147909A1 (en) | 1985-07-10 |
| EP0147909B1 (en) | 1989-12-06 |
| ES544169A0 (es) | 1987-01-16 |
| IL70823A (en) | 1987-10-20 |
| ES8802021A1 (es) | 1987-01-16 |
| JPS60123466A (ja) | 1985-07-02 |
| DK52784A (da) | 1985-06-06 |
| PT78090A (en) | 1984-03-01 |
| ATE48413T1 (de) | 1989-12-15 |
| AU2397684A (en) | 1985-06-13 |
| KR900005133B1 (ko) | 1990-07-20 |
| HU193719B (en) | 1987-11-30 |
| DE3480651D1 (de) | 1990-01-11 |
| PT78090B (en) | 1986-04-17 |
| AU572747B2 (en) | 1988-05-12 |
| US4547514A (en) | 1985-10-15 |
| ZA84697B (en) | 1984-09-26 |
| HUT35648A (en) | 1985-07-29 |
| ES8802572A1 (es) | 1987-07-01 |
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