RU99106157A - ACYLAMINOALKENYLENE-AMID DERIVATIVES AS ANTAGONISTS OF NK1 AND NK2 RECEPTORS - Google Patents
ACYLAMINOALKENYLENE-AMID DERIVATIVES AS ANTAGONISTS OF NK1 AND NK2 RECEPTORSInfo
- Publication number
- RU99106157A RU99106157A RU99106157/04A RU99106157A RU99106157A RU 99106157 A RU99106157 A RU 99106157A RU 99106157/04 A RU99106157/04 A RU 99106157/04A RU 99106157 A RU99106157 A RU 99106157A RU 99106157 A RU99106157 A RU 99106157A
- Authority
- RU
- Russia
- Prior art keywords
- phenyl
- denotes hydrogen
- denotes
- compound
- ness
- Prior art date
Links
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 title claims 3
- 108010040722 Neurokinin-2 Receptors Proteins 0.000 title claims 3
- 230000003042 antagnostic Effects 0.000 title claims 3
- 239000005557 antagonist Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 23
- 239000001257 hydrogen Substances 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- -1 1H-indole-3 -yl Chemical group 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 10
- 239000011780 sodium chloride Substances 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 150000001408 amides Chemical class 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 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 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims 2
- 102100020227 TACR2 Human genes 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000005059 halophenyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims 1
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 claims 1
- BOWUOGIPSRVRSJ-YFKPBYRVSA-N L-2-aminohexano-6-lactam Chemical compound N[C@H]1CCCCNC1=O BOWUOGIPSRVRSJ-YFKPBYRVSA-N 0.000 claims 1
- 238000007239 Wittig reaction Methods 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000005466 alkylenyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 230000002194 synthesizing Effects 0.000 claims 1
- 230000001225 therapeutic Effects 0.000 claims 1
Claims (15)
где R обозначает фенил, который не замещен или замещен 1, 2 или 3 заместителями, выбранными из группы, включающей галоген, (низш.)алкил, трифторметил, гидрокси- и (низш.)алкоксигруппу,
R1 обозначает водород или (низш.)алкил,
R2 обозначает водород, (низш.)алкил или фенил, который не замещен или замещен 1, 2 или 3 заместителями, выбранными из группы, включающей галоген, (низш.)алкил, трифторметил, гидрокси- и (низш.)алкоксигруппу,
R3 обозначает фенил, который не замещен или замещен 1, 2 или 3 заместителями, выбранными из группы, включающей галоген, (низш.)алкил, трифторметил, гидрокси- и (низш.)алкоксигруппу, или обозначает нафтил, 1H-индол-3-ил или 1-(низш.)алкилиндол-3-ил,
R'4 и R"4 каждый независимо друг от друга обозначает водород или (низш. )алкил, причем по крайней мере один из радикалов R'4 и R"4 обозначает водород, и
R5 обозначает С3-С8циклоалкил, D-азациклогептан-2-он-3-ил или L-азациклогептан-2-он-3-ил, или его соль.1. The compound of formula I
where R denotes phenyl, which is unsubstituted or substituted by 1, 2 or 3 substituents selected from the group comprising halogen, (ness.) alkyl, trifluoromethyl, hydroxy- and (ness.) alkoxy,
R 1 denotes hydrogen or (ness.) Alkyl,
R 2 denotes hydrogen, (ness.) Alkyl or phenyl, which is unsubstituted or substituted by 1, 2 or 3 substituents selected from the group including halogen, (ness.) Alkyl, trifluoromethyl, hydroxy- and (ness.) Alkoxy,
R 3 denotes phenyl which is unsubstituted or substituted with 1, 2 or 3 substituents selected from the group comprising halogen, lower alkyl, trifluoromethyl, hydroxy and lower alkoxy, or naphthyl, 1H-indole-3 -yl or 1- (ness.) alkylindol-3-yl,
R ' 4 and R " 4 each independently of the other denotes hydrogen or (ness.) Alkyl, and at least one of the radicals R' 4 and R" 4 denotes hydrogen, and
R 5 is C 3 -C 8 cycloalkyl, D-azacycloheptan-2-one-3-yl or L-azacycloheptan-2-one-3-yl, or its salt.
R обозначает фенил, 3,5-бистрифторметилфенил или 3,4,5-триметоксифенил,
R1 обозначает водород или (низш.)алкил,
R2 обозначает водород или фенил,
R3 обозначает фенил, галоидфенил, дигалоидфенил, тригалоидфенил, 2-нафтил, 1H-индол-3-ил или 1-(низш.)алкилиндол-3-ил,
R'4 и R"4 каждый независимо друг от друга обозначает водород или (низш. )алкил, причем по крайней мере один из радикалов R'4 и R"4 обозначает водород, и
R5 обозначает С5-С7циклоалкил, D-азациклогептан-2-он-3-ил или L-азациклогептан-2-он-3-ил,
или его соль.2. The compound of formula I according to claim 1, where
R is phenyl, 3,5-bistrifluoromethylphenyl or 3,4,5-trimethoxyphenyl,
R 1 denotes hydrogen or (ness.) Alkyl,
R 2 denotes hydrogen or phenyl,
R 3 denotes phenyl, halo-phenyl, dihalo-phenyl, trihalo-phenyl, 2-naphthyl, 1H-indol-3-yl or 1- (lower) alkylindol-3-yl,
R ' 4 and R " 4 each independently of the other denotes hydrogen or (ness.) Alkyl, and at least one of the radicals R' 4 and R" 4 denotes hydrogen, and
R 5 is C 5 -C 7 cycloalkyl, D-azacycloheptan-2-one-3-yl or L-azacycloheptan-2-one-3-yl,
or its salt.
R обозначает фенил, 3,5-бистрифторметилфенил или 3,4,5-триметоксифенил,
R1 обозначает водород или (низш.)алкил,
R2 обозначает водород или фенил,
R3 обозначает фенил, галоидфенил, дигалоидфенил, 2-нафтил, 1H-индол-3-ил или 1-(низш.)алкилиндол-3-ил,
R'4 и R"4 каждый независимо друг от друга обозначает водород или (низш. )алкил, причем по крайней мере один из радикалов R'4 и R"4 обозначает водород, и
R5 обозначает С5-С7циклоалкил, D-азациклогептан-2-он-3-ил или L-азациклогептан-2-он-3-ил,
или его соль.3. The compound of formula I according to claim 1, where
R is phenyl, 3,5-bistrifluoromethylphenyl or 3,4,5-trimethoxyphenyl,
R 1 denotes hydrogen or (ness.) Alkyl,
R 2 denotes hydrogen or phenyl,
R 3 denotes phenyl, halo-phenyl, dihalo-phenyl, 2-naphthyl, 1H-indol-3-yl or 1- (lower) alkylindol-3-yl,
R ' 4 and R " 4 each independently of the other denotes hydrogen or (ness.) Alkyl, and at least one of the radicals R' 4 and R" 4 denotes hydrogen, and
R 5 is C 5 -C 7 cycloalkyl, D-azacycloheptan-2-one-3-yl or L-azacycloheptan-2-one-3-yl,
or its salt.
R обозначает 3,5-бистрифторметилфенил,
R1 обозначает водород, метил или этил,
R2 обозначает водород или фенил,
R3 обозначает фенил, 4-хлорфенил, 4-фторфенил, 3,4-дихлорфенил, 3,4-дифторфенил, 3-фтор-4-хлорфенил, 3,4,5-трифторфенил, 2-нафтил, 1H-индол-3-ил или 1-метилиндол-3-ил,
R'4 и R"4 каждый независимо друг от друга обозначает водород или метил, причем по крайней мере один из радикалов R'4 и R"4 обозначает водород, и
R5 обозначает циклогексил, D-азациклогептан-2-он-3-ил или L-азациклогеп-тан-2-он-3-ил,
или его фармацевтически приемлемая соль.4. The compound of formula I according to claim 1, where
R is 3,5-bistrifluoromethylphenyl,
R 1 denotes hydrogen, methyl or ethyl,
R 2 denotes hydrogen or phenyl,
R 3 denotes phenyl, 4-chlorophenyl, 4-fluorophenyl, 3,4-dichlorophenyl, 3,4-difluorophenyl, 3-fluoro-4-chlorophenyl, 3,4,5-trifluorophenyl, 2-naphthyl, 1H-indole-3 -yl or 1-methylindol-3-yl,
R ′ 4 and R ″ 4 each independently of one another denotes hydrogen or methyl, wherein at least one of the radicals R ′ 4 and R ″ 4 denotes hydrogen, and
R 5 denotes cyclohexyl, D-azacycloheptan-2-one-3-yl or L-azacyclohepan-2-one-3-yl,
or its pharmaceutically acceptable salt.
R обозначает 3,5-бистрифторметилфенил,
R1 обозначает водород или метил,
R2 обозначает водород или фенил,
R3 обозначает фенил, 4-хлорфенил, 3,4-дихлорфенил, 2-нафтил, 1H-индол-3-ил или 1-метилиндол-3-ил,
R'4 и R"4 каждый независимо друг от друга обозначает водород или метил, причем по крайней мере один из радикалов R'4 и R"4 обозначает водород, и
R5 обозначает циклогексил, D-азациклогептан-2-он-3-ил или L-азациклогептан-2-он-3-ил,
или его фармацевтически приемлемая соль.5. The compound of formula I according to claim 1, where
R is 3,5-bistrifluoromethylphenyl,
R 1 denotes hydrogen or methyl,
R 2 denotes hydrogen or phenyl,
R 3 denotes phenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-naphthyl, 1H-indol-3-yl or 1-methylindol-3-yl,
R ′ 4 and R ″ 4 each independently of one another denotes hydrogen or methyl, wherein at least one of the radicals R ′ 4 and R ″ 4 denotes hydrogen, and
R 5 is cyclohexyl, D-azacycloheptan-2-one-3-yl or L-azacycloheptan-2-one-3-yl,
or its pharmaceutically acceptable salt.
R обозначает 3,5-бистрифторметилфенил,
R1 обозначает водород или метил,
R2 обозначает водород или фенил,
R3 обозначает фенил, 4-хлорфенил, 3,4-дихлорфенил, 2-нафтил, 1H-индол-3-ил или 1-метилиндол-3-ил,
R'4 и R"4 обозначают водород, и
R5 обозначает циклогексил, D-азациклогептан-2-он-3-ил или L-азациклогептан-2-он-3-ил,
или его фармацевтически приемлемая соль.6. The compound of formula I according to claim 1, where
R is 3,5-bistrifluoromethylphenyl,
R 1 denotes hydrogen or methyl,
R 2 denotes hydrogen or phenyl,
R 3 denotes phenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-naphthyl, 1H-indol-3-yl or 1-methylindol-3-yl,
R ' 4 and R " 4 denote hydrogen, and
R 5 is cyclohexyl, D-azacycloheptan-2-one-3-yl or L-azacycloheptan-2-one-3-yl,
or its pharmaceutically acceptable salt.
(A) N-ацилирование соединения формулы II
карбоновой кислотой R-C(=O)-OH или ее реакционноспособным производным, или
(Б) конденсацию карбоновой кислоты формулы III
или ее реакционноспособного производного с С3-С8циклоалкиламином или D(+)- или L(-)-3-амино-ε-капролактамом, или
(В) в качестве последней стадии синтез двойной связи по реакции Виттига или ее варианта, например, по реакции Виттига-Хорнера, и при необходимости превращение соединения формулы I в различные соединения формулы I и/или при необходимости превращение образовавшейся соли в свободное соединение или в различные соли, и/или при необходимости превращение образовавшегося свободного соединения формулы I, обладающего способностью образовывать соль, в соль, и/или при необходимости разделение образовавшейся смеси стереоизомеров, диастереоизомеров или энантиомеров на отдельные стереоизомеры, диастереоизомеры или энантиомеры.15. The method of obtaining the compounds of formula I under item 1, including
(A) N-acylation of a compound of formula II
carboxylic acid RC (= O) -OH or its reactive derivative, or
(B) the condensation of the carboxylic acid of formula III
or its reactive derivative with C 3 -C 8 cycloalkylamine or D (+) - or L (-) - 3-amino-ε-caprolactam, or
(B) as the last stage, the synthesis of a double bond by the Wittig reaction or its variant, for example, by the Wittig-Horner reaction, and if necessary, the conversion of a compound of formula I into various compounds of formula I and / or, if necessary, the conversion of the resulting salt into a free compound or various salts, and / or, if necessary, the conversion of the resulting free compound of formula I, which is capable of forming a salt, into a salt, and / or, if necessary, the separation of the resulting mixture of stereoisomers, diastereoisomers Whether enantiomers into the individual stereoisomers, diastereoisomers or enantiomers.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH206196 | 1996-08-22 | ||
CH2061/96 | 1996-08-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU99106157A true RU99106157A (en) | 2001-01-20 |
RU2185375C2 RU2185375C2 (en) | 2002-07-20 |
Family
ID=4225003
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU99106157/04A RU2185375C2 (en) | 1996-08-22 | 1997-08-13 | Acylaminoalkenyleneamide derivatives, methods of their synthesis and pharmaceutical composition based on thereof |
Country Status (32)
Country | Link |
---|---|
US (1) | US6319917B1 (en) |
EP (1) | EP0923550B1 (en) |
JP (1) | JP3654908B2 (en) |
KR (1) | KR100467402B1 (en) |
CN (1) | CN1119328C (en) |
AR (1) | AR009266A1 (en) |
AT (1) | ATE224875T1 (en) |
AU (1) | AU721850B2 (en) |
BR (1) | BR9711350A (en) |
CA (1) | CA2264065C (en) |
CO (1) | CO4900047A1 (en) |
CZ (1) | CZ294233B6 (en) |
DE (1) | DE69715886T2 (en) |
DK (1) | DK0923550T3 (en) |
ES (1) | ES2184083T3 (en) |
HK (1) | HK1021372A1 (en) |
HU (1) | HU226395B1 (en) |
ID (1) | ID18059A (en) |
IL (1) | IL128631A (en) |
MY (1) | MY132550A (en) |
NO (1) | NO312292B1 (en) |
NZ (1) | NZ334736A (en) |
PE (1) | PE107498A1 (en) |
PL (1) | PL193731B1 (en) |
PT (1) | PT923550E (en) |
RU (1) | RU2185375C2 (en) |
SI (1) | SI0923550T1 (en) |
SK (1) | SK283991B6 (en) |
TR (1) | TR199900363T2 (en) |
TW (1) | TW438777B (en) |
WO (1) | WO1998007694A1 (en) |
ZA (1) | ZA977493B (en) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
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US6281300B1 (en) * | 1998-03-20 | 2001-08-28 | Exxon Chemical Patents, Inc. | Continuous slurry polymerization volatile removal |
GB0010958D0 (en) * | 2000-05-05 | 2000-06-28 | Novartis Ag | Organic compounds |
GB0203061D0 (en) * | 2002-02-08 | 2002-03-27 | Novartis Ag | Organic compounds |
GB0224788D0 (en) * | 2002-10-24 | 2002-12-04 | Novartis Ag | Organic compounds |
GB2394417A (en) * | 2002-10-24 | 2004-04-28 | Novartis Ag | Solid dispersion comprising a piperidine substance P antagonist and a carrier |
BRPI0415923A (en) | 2003-10-27 | 2006-12-26 | Novartis Ag | use of neurokinin antagonists in the treatment of urinary incontinence |
TWI356821B (en) * | 2003-12-01 | 2012-01-21 | Cambridge Entpr Ltd | Anti-inflammatory agents |
GB0402679D0 (en) * | 2004-02-06 | 2004-03-10 | Novartis Ag | Organic compounds |
JO2630B1 (en) * | 2006-04-13 | 2012-06-17 | نوفارتيس ايه جي | Organic Compounds |
GB0607532D0 (en) * | 2006-04-13 | 2006-05-24 | Novartis Ag | Organic compounds |
EP1938804A1 (en) * | 2006-12-22 | 2008-07-02 | Novartis AG | Pharmaceutical formulation comprising neurokinin antagonist |
CN101641099A (en) | 2007-01-24 | 2010-02-03 | 葛兰素集团有限公司 | Pharmaceutical compositions comprising 3, 5-diamin0-6- (2, 3-dichl0phenyl) -l, 2, 4-triazine or r (-) -2, 4-diamino-5- (2, 3-dichlorophenyl) -6-fluoromethyl pyrimidine and an nk1 |
UA105182C2 (en) | 2008-07-03 | 2014-04-25 | Ньюрексон, Інк. | Benzoxazines, benzothiazines, and related compounds having nos inhibitory activity |
US20120077803A1 (en) * | 2009-02-24 | 2012-03-29 | Novartis Ag | Uses Of NK Receptor Antagonists |
RU2697414C1 (en) * | 2018-05-11 | 2019-08-14 | Общество с ограниченной ответственностью "АЙ БИ ДИ Терапевтикс" | Novel tachykinin receptor antagonist and use thereof |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CA2110514A1 (en) | 1991-07-05 | 1993-01-21 | Raymond Baker | Aromatic compounds, pharmaceutical compositions containing them and their use in therapy |
MY110227A (en) * | 1991-08-12 | 1998-03-31 | Ciba Geigy Ag | 1-acylpiperindine compounds. |
US5217996A (en) | 1992-01-22 | 1993-06-08 | Ciba-Geigy Corporation | Biaryl substituted 4-amino-butyric acid amides |
EP0716077A1 (en) * | 1994-12-08 | 1996-06-12 | Ciba-Geigy Ag | Aromatically substituted omega amino alcanoic acid amides and alcanoic diamides and their use as renine inhibitors |
TR199700834T1 (en) | 1995-02-22 | 1998-01-21 | Novartis Ag | 1-Aryl-2-Acylamino ethane compounds and their use as neurokinin, particularly as neurokinin 1 antagonists. |
-
1997
- 1997-08-08 MY MYPI97003625A patent/MY132550A/en unknown
- 1997-08-13 BR BR9711350A patent/BR9711350A/en not_active IP Right Cessation
- 1997-08-13 CZ CZ1999581A patent/CZ294233B6/en not_active IP Right Cessation
- 1997-08-13 PT PT97918984T patent/PT923550E/en unknown
- 1997-08-13 CA CA002264065A patent/CA2264065C/en not_active Expired - Fee Related
- 1997-08-13 SK SK221-99A patent/SK283991B6/en not_active IP Right Cessation
- 1997-08-13 NZ NZ334736A patent/NZ334736A/en not_active IP Right Cessation
- 1997-08-13 IL IL12863197A patent/IL128631A/en not_active IP Right Cessation
- 1997-08-13 JP JP51037198A patent/JP3654908B2/en not_active Expired - Lifetime
- 1997-08-13 AT AT97918984T patent/ATE224875T1/en active
- 1997-08-13 SI SI9730413T patent/SI0923550T1/en unknown
- 1997-08-13 ES ES97918984T patent/ES2184083T3/en not_active Expired - Lifetime
- 1997-08-13 EP EP97918984A patent/EP0923550B1/en not_active Expired - Lifetime
- 1997-08-13 DK DK97918984T patent/DK0923550T3/en active
- 1997-08-13 DE DE69715886T patent/DE69715886T2/en not_active Expired - Lifetime
- 1997-08-13 KR KR10-1999-7001487A patent/KR100467402B1/en not_active IP Right Cessation
- 1997-08-13 HU HU0001165A patent/HU226395B1/en not_active IP Right Cessation
- 1997-08-13 TR TR1999/00363T patent/TR199900363T2/en unknown
- 1997-08-13 AU AU42993/97A patent/AU721850B2/en not_active Ceased
- 1997-08-13 RU RU99106157/04A patent/RU2185375C2/en not_active IP Right Cessation
- 1997-08-13 CN CN97198633A patent/CN1119328C/en not_active Expired - Fee Related
- 1997-08-13 WO PCT/EP1997/004436 patent/WO1998007694A1/en active IP Right Grant
- 1997-08-19 AR ARP970103747A patent/AR009266A1/en active IP Right Grant
- 1997-08-20 PE PE1997000741A patent/PE107498A1/en not_active Application Discontinuation
- 1997-08-20 ID IDP972913A patent/ID18059A/en unknown
- 1997-08-21 CO CO97048265A patent/CO4900047A1/en unknown
- 1997-08-21 ZA ZA977493A patent/ZA977493B/en unknown
- 1997-08-22 TW TW086111854A patent/TW438777B/en not_active IP Right Cessation
-
1999
- 1999-02-19 PL PL97331740A patent/PL193731B1/en not_active IP Right Cessation
- 1999-02-19 NO NO19990786A patent/NO312292B1/en not_active IP Right Cessation
- 1999-12-21 HK HK99106019A patent/HK1021372A1/en not_active IP Right Cessation
-
2000
- 2000-09-05 US US09/655,170 patent/US6319917B1/en not_active Expired - Fee Related
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