KR890009870A - 피페리디닐 화합물 - Google Patents
피페리디닐 화합물 Download PDFInfo
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- KR890009870A KR890009870A KR1019880016691A KR880016691A KR890009870A KR 890009870 A KR890009870 A KR 890009870A KR 1019880016691 A KR1019880016691 A KR 1019880016691A KR 880016691 A KR880016691 A KR 880016691A KR 890009870 A KR890009870 A KR 890009870A
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- -1 Piperidinyl compound Chemical class 0.000 title claims 13
- 150000001875 compounds Chemical class 0.000 claims 25
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 230000001225 therapeutic effect Effects 0.000 claims 4
- 206010003119 arrhythmia Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 claims 2
- 230000006793 arrhythmia Effects 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 206010003225 Arteriospasm coronary Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000003890 Coronary Vasospasm Diseases 0.000 claims 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 claims 1
- 208000000112 Myalgia Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000003782 Raynaud disease Diseases 0.000 claims 1
- 208000012322 Raynaud phenomenon Diseases 0.000 claims 1
- 230000002411 adverse Effects 0.000 claims 1
- 239000000730 antalgic agent Substances 0.000 claims 1
- 230000001773 anti-convulsant effect Effects 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 229960003965 antiepileptics Drugs 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 201000011634 coronary artery vasospasm Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003176 neuroleptic agent Substances 0.000 claims 1
- 230000000701 neuroleptic effect Effects 0.000 claims 1
- 238000005935 nucleophilic addition reaction Methods 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
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- 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
- C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
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- 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
- C07D211/20—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 singly bound oxygen or sulphur atoms
- C07D211/22—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 singly bound oxygen or sulphur atoms by oxygen atoms
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- 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
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- 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
- C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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- 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
- C07D211/26—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 nitrogen atoms
- C07D211/28—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 nitrogen atoms to which a second hetero atom is attached
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- 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
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- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
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Abstract
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Description
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Claims (18)
- 다음 일반식(Ⅰ)의 화합물 및 약제학적으로 허용되는 이의 산부가염.상기식에서, Y는 H, CO(CH2)nCH3(여기에서 n은 0 내지 3의 정수이다) 또는 S02(CH2)nCH3(여기에서 n은 0 내지 3의 정수이다)이고; X는 CO, CHOH 또는 C=N-O-A(여기에서, A는 수소 또는 C1-4알킬이다)이며; R은 할로겐, 저급알킬그룹, 저급 알콕시그룹, 및 수소로 이루어진 그룹으로부터 선택되거나, 2가 치환체로 3,4-메틸렌디옥시 또는 3,4-에틸렌디옥시치환체를 나타내며; m은 1 내지 5의 정수이며, 단 X가 CO 또는 CHOH인 경우 Y는 S02(CH2)nCH3가 아니다.
- 부정맥 질환을 치료하거나 부정맥질환의 발명을 예방하기에 충분한 양의 제1항에 따른 화합물을 이를 필요로 하는 환자에게 투여함을 특징으로 하여 심부정맥을 예방하거나 치료하는 방법.
- 제1항에 있어서, X가 C=N-O-A인 화합물.
- 진통제로 유효한 양의 일반식(Ⅰ)화합물 및 약제학적으로 허용되는 이의 산부가염을, 이를 필요로 하는 환자에게 투여함을 특징을로 하여 통증을 해소하거나 경감시키는 방법:상기식에서 Y는 H,CO(CH2)nCH3(여기에서 n은 0 내지 3의 정수이다) 또는 S02(CH2)nCH3(여기에서 n은 0 내지 3의 정수이다)이고; X는 CO, CHOH 또는 C=N-O-A(여기에서, A는 수소 또는 C1-4알킬이다)이며; R은 할로겐, 저급알킬그룹, 저급 알콕시그룹, 및 수소로 이루어진 그룹으로부터 선택되거나, 이가 치환체로 3,4-메틸렌디옥시 또는 3,4-에틸렌디옥시치환체를 나타내며; m은 1 내지 5의 정수이다.
- 불안해소량의 제4항에 따른 화합물을 이를 필요로 하는 환자에게 투여함을 특징으로 하여 불안을 해소시키거나 경감시키는 방법.
- 협심증 치료량의 제4항에 따른 화합물을 이를 필요로 하는 환자에게 투여함을 특징으로 하여 여러가지 협심증을 치료하는 방법.
- 식욕 불량 치료량의 제4항에 따른 화합물을 이를 필요로 하는 환자에게 투여함을 특징으로 하여 신경성 식욕불량을 치료하는 방법.
- 환자의 증후군을 해소하거나 경감시키기에 충분한 양의 제4항에 따른 화합물을 이를 필요로 하는 환자에게 투여함을 특징으로 하여 레이노 현상을 치료하는 방법.
- 경련 치료량의 제4항에 따른 화합물을 이를 필요로 하는 환자에게 투여함을 특징으로 하여 관상 혈관 경련을 치료하는 방법.
- 혈전증치료량의 제4항에 따른 화합물을 이를 필요로 하는 환자에게 투여함을 특징으로 하여 혈전붕괴성질환을 치료하는 방법.
- 섬유성근통증의 제4항에 따른 화합물을 이를 필요로 하는 환자에게 투여함을 특징으로 하여 섬유성 근통증을 치료하는 방법.
- EPS치료량의 제4항에 따른 화합물을 이를 필요로 하는 환자에게 투여함을 특징으로 하여 신경이완 치료와 관련된 추체외로의 부작용을 치료하는 방법.
- 일반식(Ⅳ)의 중간체 화합물.상기식에서 Y는 H,CO(CH2)nCH3(여기에서 n은 0 내지 3의 정수이다) 또는 S02(CH2)nCH3(여기에서 n은 0 내지 3의 정수이다)이고; X는 CO, CHOH 또는 C=N-O-A(여기에서, A는 수소 또는 C1-4알킬이다)이며, 단 X가 CO 또는 CHOH인 경우 Y는 S02(CH2)nCH3가 아니다.
- 수축력을 증가시키는 양의 하기 일반식의 화합물을 이를 필요로하는 환자에게 투여함을 특징으로 하여 심장 수축력을 증가시키는 방법.상기식에서, R, m 및 n은 제1항에서 정의한 바와 같고, R1은 C1-6알킬이며, P는 1 내지 6의 정수이다.
- a) 일반식(Ⅱ)와 일반식(Ⅲ)의 화합물간에 프리델 크라프트(Friedel-Crafts)아실화 반응을 수행하고; b) 단계 (a)에서 수득된 생성물을 일반식(Ⅳ)의 화합물과 반응시킴을 특징으로하여, 일반식(Ⅰ-1)의 화합물 및 약제학적으로 허용되는 이의 산 부가염을 제조하는 방법.상기식에서 Y는 H, CO(CH2)nCH3(여기에서 n은 0 내지 3의 정수이다) 또는 S02(CH2)nCH3(여기에서 n은 0 내지 3의 정수이다)이고, R은 할로겐, 저급알킬그룹, 저급알콕시그룹, 및 수소로 이루어진 그룹으로부터 선택되거나, 2가 치환체로 3,4-메틸렌디옥시 또는 3,4-에틸렌디옥시그룹이며, m은 1 내지 5의 정수이고, Z는 브롬, 염소 및 요오드로부터 선택된 할로겐 원자이다.
- a) 일반식(Ⅰ-1)의 화합물을 환원시키거나, b) 일반식(Ⅳ)의 화합물을 환원시키고, 환원된 생성물을 일반식(Ⅴ)의 화합물과 반응시킴을 특징으로하여, 일반식 (Ⅱ-2)의 화합물 및 약제학적으로 허용되는 이의 산부가염을 제조하는 방법.상기식에서 Y는 H, CO(CH2)nCH3(여기에서 n은 0 내지 3의 정수이다) 또는 S02(CH2)nCH3(여기에서 n은 0 내지 3의 정수이다)이고, R은 할로겐, 저급알킬그룹, 저급알콕시그룹, 및 수소로 이루어진 그룹으로부터 선택되거나, 2가 치환체로 3,4-메틸렌디옥시 또는 3,4-에틸렌디옥시그룹이며, m은 1 내지 5의 정수이고, Z는 Br, C1 또는 Ⅰ이다.
- 일반식(Ⅰ-1)의 화합물과 NH2-O-A-화합물간에 친핵성 부가반응을 수행함을 특징으로 하여 일반식(Ⅰ-3)의 화합물 및 약제학적으로 허용되는 이의 산부가염을 제조하는 방법.상기식에서 Y는 H, CO(CH2)nCH3(여기에서 n은 0 내지 3의 정수이다) 또는 S02(CH2)nCH3(여기에서 n은 0 내지 3의 정수이다)이고, A는 H 또는 C1-4알킬이며, R은 할로겐, 저급알킬그룹, 저급 알콕시그룹, 및 수소로 이루어진 그룹으로부터 선택되거나, 2가 치환체로 3,4-메틸렌디옥시 또는 3,4-에틸렌디옥시치환체를 나타내며; m은 1 내지 5의 정수이다.
- 일반식(Ⅰ-4)의 화합물을 가수분해시킴을 특징으로 하여 일반식(Ⅰ-5)의 화합물 및 약제학적으로 허용되는 이의 산부가염을 제조하는 방법.상기식에서 X는 CO, CHOH 또는 C=N-O-A(여기에서, A는 수소 또는 C1-4알킬이다)이고, R은 할로겐, 저급알킬그룹, 저급 알콕시그룹, 및 수소로 이루어진 그룹으로부터 선택되거나, 2가 치환체로 3,4-메틸렌디옥시 또는 3,4-에틸렌디옥시그룹이고, m은 1 내지 5의 정수이다.※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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US13440687A | 1987-12-17 | 1987-12-17 | |
US134,406 | 1987-12-17 | ||
US237,600 | 1988-08-26 | ||
US07/237,600 US5093341A (en) | 1987-12-17 | 1988-08-26 | N-aralkyl piperidine derivatives useful as antithrombolytic agents |
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KR890009870A true KR890009870A (ko) | 1989-08-04 |
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KR1019880016691A KR890009870A (ko) | 1987-12-17 | 1988-12-15 | 피페리디닐 화합물 |
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US (1) | US5093341A (ko) |
EP (1) | EP0320983B1 (ko) |
JP (1) | JP2835731B2 (ko) |
KR (1) | KR890009870A (ko) |
CN (1) | CN1033805A (ko) |
AR (1) | AR246257A1 (ko) |
AT (1) | ATE124397T1 (ko) |
AU (1) | AU612743B2 (ko) |
CA (1) | CA1322007C (ko) |
DE (1) | DE3854077T2 (ko) |
DK (1) | DK173764B1 (ko) |
ES (1) | ES2076155T3 (ko) |
FI (1) | FI885827A (ko) |
GR (1) | GR3017481T3 (ko) |
HU (2) | HUT52051A (ko) |
IE (1) | IE66733B1 (ko) |
IL (1) | IL88682A0 (ko) |
NO (1) | NO174503B (ko) |
NZ (1) | NZ227323A (ko) |
PH (1) | PH27519A (ko) |
PT (1) | PT89249B (ko) |
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JPH02138214A (ja) * | 1987-12-10 | 1990-05-28 | Merrell Dow Pharmaceut Inc | 不安を治療する方法 |
ZA891901B (en) * | 1988-03-17 | 1989-11-29 | Merrell Dow Pharma | Method for the treatment of the extrapyramidal side effects associated with neuroleptic therapy |
JP2969359B2 (ja) * | 1989-01-13 | 1999-11-02 | 武田薬品工業株式会社 | 環状アミン化合物 |
NZ236501A (en) * | 1989-12-21 | 1992-12-23 | Merrell Dow Pharma | Piperidine derivatives and antithrombotic compositions |
US5292752A (en) * | 1989-12-21 | 1994-03-08 | Merrell Dow Pharmaceuticals Inc. | Antithrombotic compounds |
AU652759B2 (en) * | 1990-06-01 | 1994-09-08 | Aventisub Ii Inc. | (+)-alpha-(2,3-dimethoxyphenyl)-1-(2-(4-fluorophenyl)ethyl)- 4-piperidinemethanol |
US5478846A (en) * | 1990-06-07 | 1995-12-26 | Merrell Dow Pharmaceuticals Inc. | 1-piperidinyl alkanoylanyl sulfonamides for treatment of cardiac arrhythmia |
DE69123052T2 (de) * | 1990-06-07 | 1997-03-06 | Merrell Pharmaceuticals Inc., Cincinnati, Ohio | Derivate des 1-piperidinyl-alkanoylarylsulfonamids |
US5202346A (en) * | 1992-02-25 | 1993-04-13 | American Home Products Corporation | Piperidinyl and piperazinyl derivatives |
US5254689A (en) * | 1992-02-25 | 1993-10-19 | American Home Products Corporation | Piperdinyl and piperazinyl derivatives |
EP0661266A1 (en) * | 1993-12-27 | 1995-07-05 | Toa Eiyo Ltd. | Substituted cyclic amine compounds as 5HT2 antagonists |
DE19934433A1 (de) | 1999-07-22 | 2001-01-25 | Merck Patent Gmbh | N-(Indolcarbonyl-)piperazinderivate |
DE19939756A1 (de) * | 1999-08-21 | 2001-02-22 | Merck Patent Gmbh | Piperidinalkohole |
CN100384836C (zh) | 2000-02-29 | 2008-04-30 | 三菱制药株式会社 | 新型环状酰胺衍生物 |
US6914142B2 (en) * | 2001-10-15 | 2005-07-05 | Schering Corporation | Synthesis of (4-bromopnenyl)(4-piperidyl)methanone-(Z)-O-ethyloxime and salts |
DE10201550A1 (de) * | 2002-01-17 | 2003-07-31 | Merck Patent Gmbh | Phenoxy-Piperidine |
DE102004010132A1 (de) * | 2004-02-27 | 2005-09-15 | Merck Patent Gmbh | Piperidinderivate |
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US3632767A (en) * | 1968-02-12 | 1972-01-04 | Mallinckrodt Chemical Works | Treatment of depression with 4-substituted piperidines |
US3576810A (en) * | 1968-06-20 | 1971-04-27 | Robins Co Inc A H | 1-substituted-3-(-4)-aroylpiperidines |
FR2581993B1 (fr) * | 1985-05-14 | 1988-03-18 | Synthelabo | Derives de (benzoyl-4 piperidino)-2 phenyl-1 alcanols, leur preparation et leur application en therapeutique |
CA1280421C (en) * | 1985-07-02 | 1991-02-19 | Albert A. Carr | 1,4-disubstituted piperidinyl derivatives |
US4783471A (en) * | 1985-07-02 | 1988-11-08 | Merrell Dow Pharmaceuticals Inc. | N-aralkyl piperidine methanol derivatives and the uses thereof |
PH23283A (en) * | 1986-02-26 | 1989-06-30 | Eisai Co Ltd | Piperidine derivative, pharmaceutical composition containing the same and method of use thereof |
US4870083A (en) * | 1987-11-24 | 1989-09-26 | Merrell Dow Pharmaceuticals Inc. | 1,4-Disubstituted-piperidinyl compounds useful as analgesics and muscle relaxants |
JPH02138214A (ja) * | 1987-12-10 | 1990-05-28 | Merrell Dow Pharmaceut Inc | 不安を治療する方法 |
-
1988
- 1988-08-26 US US07/237,600 patent/US5093341A/en not_active Expired - Fee Related
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- 1988-12-14 IL IL88682A patent/IL88682A0/xx not_active IP Right Cessation
- 1988-12-15 AR AR88312746A patent/AR246257A1/es active
- 1988-12-15 DK DK198806980A patent/DK173764B1/da not_active IP Right Cessation
- 1988-12-15 KR KR1019880016691A patent/KR890009870A/ko not_active Application Discontinuation
- 1988-12-16 IE IE376288A patent/IE66733B1/en not_active IP Right Cessation
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- 1988-12-16 CN CN88108620A patent/CN1033805A/zh active Pending
- 1988-12-16 JP JP63316632A patent/JP2835731B2/ja not_active Expired - Fee Related
- 1988-12-16 DE DE3854077T patent/DE3854077T2/de not_active Expired - Fee Related
- 1988-12-16 EP EP88121138A patent/EP0320983B1/en not_active Expired - Lifetime
- 1988-12-16 AT AT88121138T patent/ATE124397T1/de not_active IP Right Cessation
- 1988-12-16 CA CA000586190A patent/CA1322007C/en not_active Expired - Fee Related
- 1988-12-16 ES ES88121138T patent/ES2076155T3/es not_active Expired - Lifetime
- 1988-12-16 HU HU886478A patent/HU202493B/hu not_active IP Right Cessation
- 1988-12-16 FI FI885827A patent/FI885827A/fi not_active Application Discontinuation
- 1988-12-16 PT PT89249A patent/PT89249B/pt not_active IP Right Cessation
- 1988-12-16 AU AU27000/88A patent/AU612743B2/en not_active Ceased
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1989
- 1989-11-29 PH PH39625A patent/PH27519A/en unknown
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Also Published As
Publication number | Publication date |
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HUT52051A (en) | 1990-06-28 |
CN1033805A (zh) | 1989-07-12 |
IE883762L (en) | 1989-06-17 |
PT89249A (pt) | 1989-12-29 |
NO174503B (no) | 1994-02-07 |
JPH01197469A (ja) | 1989-08-09 |
NZ227323A (en) | 1991-01-29 |
PH27519A (en) | 1993-08-18 |
IE66733B1 (en) | 1996-01-24 |
ATE124397T1 (de) | 1995-07-15 |
AR246257A1 (es) | 1994-07-29 |
HU202493B (en) | 1991-03-28 |
DK173764B1 (da) | 2001-09-17 |
CA1322007C (en) | 1993-09-07 |
JP2835731B2 (ja) | 1998-12-14 |
DE3854077T2 (de) | 1995-11-02 |
EP0320983B1 (en) | 1995-06-28 |
HU199445B (en) | 1990-02-28 |
DK698088D0 (da) | 1988-12-15 |
DK698088A (da) | 1989-06-18 |
FI885827A0 (fi) | 1988-12-16 |
NO885607L (no) | 1989-06-19 |
PT89249B (pt) | 1993-07-30 |
NO885607D0 (no) | 1988-12-16 |
ES2076155T3 (es) | 1995-11-01 |
AU612743B2 (en) | 1991-07-18 |
HUT50121A (en) | 1989-12-28 |
FI885827A (fi) | 1989-06-18 |
EP0320983A3 (en) | 1990-10-10 |
NO174503C (ko) | 1994-05-18 |
IL88682A0 (en) | 1989-07-31 |
GR3017481T3 (en) | 1995-12-31 |
EP0320983A2 (en) | 1989-06-21 |
AU2700088A (en) | 1989-06-22 |
DE3854077D1 (de) | 1995-08-03 |
US5093341A (en) | 1992-03-03 |
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