PH26153A - Alkoxy-substituted dihydro-benzopyran-2-carboxylate derivatives pharmaceutical composition containing said compound and method of use thereof - Google Patents

Alkoxy-substituted dihydro-benzopyran-2-carboxylate derivatives pharmaceutical composition containing said compound and method of use thereof Download PDF

Info

Publication number: PH26153A
Authority: PH; Philippines
Prior art keywords: benzopyran; compound; dihydro; acetyl; methoxy
Prior art date: 1987-05-29

Application number

PH36982A

Other languages

English (en)

Inventor

Steven Wakefield Djuric

Robert Larry Shone

Stella S Yu

Original Assignee

Searle & Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-05-29

Filing date

1988-05-26

Publication date

1992-03-18

1988-05-26 Application filed by Searle & Co filed Critical Searle & Co

1992-03-18 Publication of PH26153A publication Critical patent/PH26153A/en

Links

150000001875 compounds Chemical class 0.000 title claims description 159
238000000034 method Methods 0.000 title claims description 48
239000008194 pharmaceutical composition Substances 0.000 title claims 17
125000004432 carbon atom Chemical group C* 0.000 claims description 56
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 40
125000000217 alkyl group Chemical group 0.000 claims description 39
229910052739 hydrogen Inorganic materials 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 24
-1 propoxyl-1,2,3,4-tetrahydro-8-propyl-2-naphthalene- carboxylate Chemical compound 0.000 claims description 22
208000027866 inflammatory disease Diseases 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 20
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 17
241000124008 Mammalia Species 0.000 claims description 16
150000002617 leukotrienes Chemical class 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 7
150000002431 hydrogen Chemical group 0.000 claims description 7
HMXJOWDZAJWLTF-UHFFFAOYSA-N 2h-chromene-2-carboxylic acid Chemical compound C1=CC=C2C=CC(C(=O)O)OC2=C1 HMXJOWDZAJWLTF-UHFFFAOYSA-N 0.000 claims description 6
125000004450 alkenylene group Chemical group 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
201000004681 Psoriasis Diseases 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
201000005569 Gout Diseases 0.000 claims description 4
125000004419 alkynylene group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 2
230000003110 anti-inflammatory effect Effects 0.000 claims 41
239000003937 drug carrier Substances 0.000 claims 14
230000002757 inflammatory effect Effects 0.000 claims 2
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125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
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235000019439 ethyl acetate Nutrition 0.000 description 34
239000000047 product Substances 0.000 description 31
239000002904 solvent Substances 0.000 description 28
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
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238000012360 testing method Methods 0.000 description 18
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125000004122 cyclic group Chemical group 0.000 description 16
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125000001931 aliphatic group Chemical group 0.000 description 15
238000004452 microanalysis Methods 0.000 description 15
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XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
230000027455 binding Effects 0.000 description 13
239000012267 brine Substances 0.000 description 13
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
241000700199 Cavia porcellus Species 0.000 description 12
230000000694 effects Effects 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
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235000019341 magnesium sulphate Nutrition 0.000 description 11
239000003921 oil Substances 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
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238000001914 filtration Methods 0.000 description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
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238000006243 chemical reaction Methods 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
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239000012981 Hank's balanced salt solution Substances 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
238000003556 assay Methods 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
238000011534 incubation Methods 0.000 description 8
YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
239000000556 agonist Substances 0.000 description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
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FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
239000007787 solid Substances 0.000 description 6
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239000002552 dosage form Substances 0.000 description 5
231100000673 dose–response relationship Toxicity 0.000 description 5
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
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LMQBMWHHGVZWMR-UHFFFAOYSA-N 7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropoxy]-4-oxo-8-propyl-1-benzopyran-2-carboxylic acid Chemical compound C1=CC(C(C)=O)=C(O)C(CCC)=C1OCC(O)COC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1CCC LMQBMWHHGVZWMR-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
229910002091 carbon monoxide Inorganic materials 0.000 description 4
230000035605 chemotaxis Effects 0.000 description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
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150000002148 esters Chemical class 0.000 description 4
239000010410 layer Substances 0.000 description 4
MWVNSXPNTJYJDR-DHIUTWEWSA-N n-[(2r,4r)-1,4-dihydroxy-4-phenylbutan-2-yl]tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)N[C@@H](CO)C[C@@H](O)C1=CC=CC=C1 MWVNSXPNTJYJDR-DHIUTWEWSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 3
239000012131 assay buffer Substances 0.000 description 3
NBLAIKHFQBOVPV-UHFFFAOYSA-N bis(ethoxycarbonyl)azaniumylideneazanide Chemical compound CCOC(=O)[N+](=[N-])C(=O)OCC NBLAIKHFQBOVPV-UHFFFAOYSA-N 0.000 description 3
150000007942 carboxylates Chemical class 0.000 description 3
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LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/66—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 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 in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
- A61P5/12—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH for decreasing, blocking or antagonising the activity of the posterior pituitary hormones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 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 in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4

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Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Medicinal Preparation (AREA)

PH36982A 1987-05-29 1988-05-26 Alkoxy-substituted dihydro-benzopyran-2-carboxylate derivatives pharmaceutical composition containing said compound and method of use thereof PH26153A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5713687A	1987-05-29	1987-05-29
US07/188,708 US4889871A (en)	1987-05-29	1988-05-12	Alkoxy-substituted dihydrobenzopyran-2-carboxylate derivatives

Publications (1)

Publication Number	Publication Date
PH26153A true PH26153A (en)	1992-03-18

Family

ID=26736113

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH36982A PH26153A (en)	1987-05-29	1988-05-26	Alkoxy-substituted dihydro-benzopyran-2-carboxylate derivatives pharmaceutical composition containing said compound and method of use thereof

Country Status (17)

Country	Link
US (1)	US4889871A (da)
EP (1)	EP0292977B1 (da)
JP (1)	JP2758902B2 (da)
KR (1)	KR880013914A (da)
AU (1)	AU611153B2 (da)
CA (1)	CA1337660C (da)
DE (1)	DE3864582D1 (da)
DK (1)	DK290188A (da)
ES (1)	ES2051796T3 (da)
FI (1)	FI882505A7 (da)
GR (1)	GR3003177T3 (da)
IE (1)	IE60687B1 (da)
IL (1)	IL86502A (da)
NO (1)	NO171063C (da)
NZ (1)	NZ224807A (da)
PH (1)	PH26153A (da)
PT (1)	PT87603B (da)

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US5380740A (en) *	1993-04-28	1995-01-10	G. D. Searle & Co.	Anti-inflammatory compounds, compositions and method of use thereof
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US5457124A (en) *	1993-12-07	1995-10-10	Hoffmann-La Roche Inc.	Carboxylic acid Leukotriene B4 antagonists
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US5516917A (en) *	1994-06-08	1996-05-14	G. D. Searle & Co.	Leukotriene B4 antagonists
JPH10505348A (ja) *	1994-08-31	1998-05-26	イーライ・リリー・アンド・カンパニー	耐性腫瘍の同定および治療方法
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KR100232340B1 (ko) *	1994-10-13	1999-12-01	디. 제이. 우드, 스피겔 알렌 제이	류코트리엔 b4(ltb4) 길항물질로서의 벤조피란 및 벤조-축합된 화합물
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1988
- 1988-05-12 US US07/188,708 patent/US4889871A/en not_active Expired - Lifetime
- 1988-05-26 PH PH36982A patent/PH26153A/en unknown
- 1988-05-26 NO NO882317A patent/NO171063C/no unknown
- 1988-05-26 NZ NZ224807A patent/NZ224807A/xx unknown
- 1988-05-26 CA CA000567806A patent/CA1337660C/en not_active Expired - Fee Related
- 1988-05-26 IL IL8650288A patent/IL86502A/en unknown
- 1988-05-26 AU AU16681/88A patent/AU611153B2/en not_active Ceased
- 1988-05-27 DK DK290188A patent/DK290188A/da not_active Application Discontinuation
- 1988-05-27 EP EP88108449A patent/EP0292977B1/en not_active Expired - Lifetime
- 1988-05-27 JP JP63130037A patent/JP2758902B2/ja not_active Expired - Fee Related
- 1988-05-27 IE IE161188A patent/IE60687B1/en not_active IP Right Cessation
- 1988-05-27 FI FI882505A patent/FI882505A7/fi not_active IP Right Cessation
- 1988-05-27 PT PT87603A patent/PT87603B/pt not_active IP Right Cessation
- 1988-05-27 KR KR1019880006263A patent/KR880013914A/ko not_active Ceased
- 1988-05-27 DE DE8888108449T patent/DE3864582D1/de not_active Expired - Fee Related
- 1988-05-27 ES ES88108449T patent/ES2051796T3/es not_active Expired - Lifetime
1991
- 1991-11-22 GR GR91401338T patent/GR3003177T3/el unknown

Also Published As

Publication number	Publication date
NO171063B (no)	1992-10-12
FI882505A0 (fi)	1988-05-27
FI882505A7 (fi)	1988-11-30
NO882317L (no)	1988-11-30
KR880013914A (ko)	1988-12-22
PT87603B (pt)	1992-12-31
US4889871A (en)	1989-12-26
IL86502A0 (en)	1988-11-15
DE3864582D1 (de)	1991-10-10
IE881611L (en)	1988-11-29
NO882317D0 (no)	1988-05-26
CA1337660C (en)	1995-11-28
EP0292977A1 (en)	1988-11-30
PT87603A (pt)	1988-06-01
IE60687B1 (en)	1994-08-10
IL86502A (en)	1994-07-31
NZ224807A (en)	1991-03-26
ES2051796T3 (es)	1994-07-01
AU611153B2 (en)	1991-06-06
DK290188A (da)	1988-11-30
JP2758902B2 (ja)	1998-05-28
JPS6438045A (en)	1989-02-08
NO171063C (no)	1993-01-20
DK290188D0 (da)	1988-05-27
AU1668188A (en)	1988-12-01
GR3003177T3 (en)	1993-02-17
EP0292977B1 (en)	1991-09-04

Publication	Publication Date	Title
EP0292977B1 (en)	1991-09-04	Alkoxy-substituted dihydrobenzopyran-2-carboxylate derivatives
CA2081766C (en)	2002-10-08	Leukotriene b4 antagonists
EP0150447B1 (en)	1990-01-24	Substituted dihydrobenzopyran-2-carboxylates
US5047431A (en)	1991-09-10	1,1,2-triphenylbut-1-ene derivatives
US4388312A (en)	1983-06-14	Quinone derivatives, their production and use
US4565818A (en)	1986-01-21	Pharmaceutically active 1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline derivatives
GB2196964A (en)	1988-05-11	(6a s, 10a s)-1-hydroxy- 8-thc derivatives
JPH0678257B2 (ja)	1994-10-05	新規なアルケン誘導体の製造法
EP0717620A4 (en)	1997-05-28	SUBSTITUTED 2-AMINOTETRALINE
JPH02502723A (ja)	1990-08-30	置換ベンゾアゼピン，それらの製法およびそれらを含有する医薬組成物
KR900003883B1 (ko)	1990-06-04	3,4-디하이드로-2h-[ 1 ]-(벤조피란 및 벤조 티오피란)-3-아민 및 이의 제조방법
AU2001236665A1 (en)	2001-11-01	Ocular hypotensive lipids
HU185133B (en)	1984-12-28	Process for producing 1-hydroxy-octahydro-benzo-bracket-c-bracket closed-quinolines and derivatives
NZ244218A (en)	1995-07-26	Benzofuran, benzopyran or naphthalene carboxylic acids; pharmaceutical compositions and preparatory methods
EP0235452A2 (en)	1987-09-09	Organic compounds and their pharmaceutical use
Salman et al.	1986	Studies in antifertility agents. 50. Stereoselective binding of d-and l-centchromans to estrogen receptors and their antifertility activity
US4791133A (en)	1988-12-13	Phenylene, furyl, and thienyl leukotriene B4 analogues
IE55991B1 (en)	1991-03-13	Bicyclic benzo fused compounds
US4533554A (en)	1985-08-06	Quinone derivatives and use
US4312861A (en)	1982-01-26	Pharmaceutical compositions containing N-alkyl-N-(nuclearly-substituted) benzylamines having vasotonia-regulating activity
CA1326675C (fr)	1994-02-01	Derives trieniques de structure chromenique, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
AU5555290A (en)	1990-11-16	Substituted 3-amino chromans
NZ236534A (en)	1992-06-25	Method of treating inflammatory diseases
US4192868A (en)	1980-03-11	Novel aryl-hexafuranosides and processes for their preparation
CA1220787A (en)	1987-04-21	1,1,2-triphenyl-but-1-ene derivatives possessing anti- oestrogenic activities