PH26157A - 6,11-dihydro-11(4-piperidylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridines and compositions and methods of use - Google Patents

6,11-dihydro-11(4-piperidylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridines and compositions and methods of use Download PDF

Info

Publication number: PH26157A
Authority: PH; Philippines
Prior art keywords: compound; alkyl; carbon atoms; halo; chloro
Prior art date: 1987-04-28

Application number

PH35970A

Other languages

English (en)

Inventor

John J Piwinski

Michael J Green

Ashit K Ganuly

Jesse K Wong

Bernard Katchen

Jeffrey Cramer

Original Assignee

Schering Corp

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.)

1987-04-28

Filing date

1987-10-22

Publication date

1992-03-18

1987-10-22 Application filed by Schering Corp filed Critical Schering Corp

1992-03-18 Publication of PH26157A publication Critical patent/PH26157A/en

Links

239000000203 mixture Substances 0.000 title claims description 51
238000000034 method Methods 0.000 title claims description 17
VEHMROQZMLRPSA-UHFFFAOYSA-N 11-piperidin-4-ylidene-5,6-dihydrobenzo[1,2]cyclohepta[3,4-b]pyridine Chemical class C1CNCCC1=C1C2=NC=CC=C2CCC2=CC=CC=C21 VEHMROQZMLRPSA-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 153
125000000217 alkyl group Chemical group 0.000 claims description 36
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
206010020751 Hypersensitivity Diseases 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
208000026935 allergic disease Diseases 0.000 claims description 5
230000007815 allergy Effects 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
239000012453 solvate Substances 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
230000003266 anti-allergic effect Effects 0.000 claims 2
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 claims 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
239000007787 solid Substances 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 20
239000002253 acid Substances 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
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238000002360 preparation method Methods 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 16
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DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000012300 argon atmosphere Substances 0.000 description 12
239000012267 brine Substances 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
229960003010 sodium sulfate Drugs 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
-1 N-substituted piperidylidene Chemical group 0.000 description 9
230000001387 anti-histamine Effects 0.000 description 9
238000010992 reflux Methods 0.000 description 9
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XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
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150000001721 carbon Chemical group 0.000 description 7
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231100000225 lethality Toxicity 0.000 description 7
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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235000019441 ethanol Nutrition 0.000 description 6
238000003818 flash chromatography Methods 0.000 description 6
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VZAWCLCJGSBATP-UHFFFAOYSA-N 1-cycloundecyl-1,2-diazacycloundecane Chemical compound C1CCCCCCCCCC1N1NCCCCCCCCC1 VZAWCLCJGSBATP-UHFFFAOYSA-N 0.000 description 5
PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 5
239000000739 antihistaminic agent Substances 0.000 description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
239000003814 drug Substances 0.000 description 5
229960004756 ethanol Drugs 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
229960001697 physostigmine Drugs 0.000 description 5
PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 5
239000011734 sodium Substances 0.000 description 5
238000010998 test method Methods 0.000 description 5
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
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239000000839 emulsion Substances 0.000 description 4
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235000013772 propylene glycol Nutrition 0.000 description 4
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238000010791 quenching Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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101710134784 Agnoprotein Proteins 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 3
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238000010511 deprotection reaction Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
229960001340 histamine Drugs 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000008101 lactose Substances 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
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235000019341 magnesium sulphate Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
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229910052708 sodium Inorganic materials 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
210000002700 urine Anatomy 0.000 description 3
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
DNXUGBMARDFRGG-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Chemical compound O=C1C=CC(=O)C(C#N)=C1C#N DNXUGBMARDFRGG-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
HZOTZTANVBDFOF-PBCQUBLHSA-N physostigmine salicylate Chemical compound OC(=O)C1=CC=CC=C1O.C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C HZOTZTANVBDFOF-PBCQUBLHSA-N 0.000 description 1
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DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 1
239000004033 plastic Substances 0.000 description 1
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pulmonology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)

PH35970A 1987-04-28 1987-10-22 6,11-dihydro-11(4-piperidylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridines and compositions and methods of use PH26157A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/043,409 US4804666A (en)	1985-08-14	1987-04-28	Antiallergic 6,11-dihydro-11-(4-piperidylidene)-5H-benzo(5,6)cyclohepta(1,2-B)pyridines

Publications (1)

Publication Number	Publication Date
PH26157A true PH26157A (en)	1992-03-18

Family

ID=21927034

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH35970A PH26157A (en)	1987-04-28	1987-10-22	6,11-dihydro-11(4-piperidylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridines and compositions and methods of use

Country Status (22)

Country	Link
US (1)	US4804666A (da)
EP (1)	EP0288640B1 (da)
JP (1)	JPH0780870B2 (da)
KR (1)	KR960009426B1 (da)
AR (1)	AR246520A1 (da)
AT (1)	ATE80394T1 (da)
AU (1)	AU612339B2 (da)
CA (1)	CA1332172C (da)
DE (1)	DE3781679T2 (da)
DK (1)	DK540789A (da)
ES (1)	ES2043665T3 (da)
FI (1)	FI96858C (da)
GR (1)	GR3006483T3 (da)
HK (1)	HK135595A (da)
HU (1)	HU202520B (da)
IE (1)	IE61740B1 (da)
IL (1)	IL84235A (da)
MX (1)	MX9203282A (da)
NZ (1)	NZ222253A (da)
PH (1)	PH26157A (da)
PT (1)	PT85975B (da)
WO (1)	WO1988008423A1 (da)

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US4826853A (en) *	1986-10-31	1989-05-02	Schering Corporation	6,11-Dihydro-11-(N-substituted-4-piperidylidene)-5H-benzo(5,6)cyclohepta(1,2-B)pyridines and compositions and methods of use
KR950004004B1 (ko) *	1988-04-28	1995-04-22	쉐링코포레이션	신규한 벤조피리도 피페리딘, 피페리딜리덴 및 피페라진 화합물, 조성물, 제조방법 및 이용방법
US5595997A (en) *	1994-12-30	1997-01-21	Sepracor Inc.	Methods and compositions for treating allergic rhinitis and other disorders using descarboethoxyloratadine
US7214683B1 (en)	1994-12-30	2007-05-08	Sepracor Inc.	Compositions of descarboethoxyloratadine
US7211582B1 (en)	1994-12-30	2007-05-01	Sepracor Inc.	Methods for treating urticaria using descarboethoxyloratadine
US5900421A (en) *	1997-02-11	1999-05-04	Sepracor Inc.	Methods and compositions for treating allergic asthma and dermatitis using descarboethoxyloratadine
CH688412A5 (de) *	1997-03-11	1997-09-15	Cilag Ag	Verfahren zur Herstellung von 1,4-disubstituierten Piperidinverbindungen.
ATE274498T1 (de) *	1998-07-24	2004-09-15	Russinsky Ltd	Verfahren zur herstellung von benzocycloheptapyridin-11-one
US6100274A (en) *	1999-07-07	2000-08-08	Schering Corporation	8-chloro-6,11-dihydro-11- ](4-piperidylidine)-5H-benzo[5,6]cyclohepta[1,2-bpyridine oral compositions
US6114346A (en) *	1999-10-22	2000-09-05	Schering Corporation	Treating sleep disorders using desloratadine
SK287684B6 (sk) *	1999-12-20	2011-06-06	Schering Corporation	Pevná orálna farmaceutická dávková forma s predĺženým uvoľňovaním
SK287105B6 (sk)	1999-12-20	2009-12-07	Schering Corporation	Dvojvrstvový orálny dávkový prostriedok s predĺženým uvoľňovaním
US7405223B2 (en)	2000-02-03	2008-07-29	Schering Corporation	Treating allergic and inflammatory conditions
US20020064555A1 (en) *	2000-09-29	2002-05-30	Dan Cullen	Proton pump inhibitor formulation
US20030228363A1 (en) *	2002-06-07	2003-12-11	Patel Mahendra R.	Stabilized pharmaceutical compositons containing benzimidazole compounds
CN102993172B (zh) *	2012-12-19	2014-04-02	天津大学	具有抗组胺活性的三环类化合物、制备方法及用途
US10532737B2 (en)	2017-05-17	2020-01-14	Ford Global Technologies, Llc	Cooperative park assist
CN109897027B (zh) *	2019-04-28	2021-11-02	梯尔希（南京）药物研发有限公司	一种3-羟基地氯雷他定代谢物的合成方法

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Publication number	Priority date	Publication date	Assignee	Title
DE1470314B2 (de) *	1963-04-24	1974-07-11	Scherico Ltd., Luzern (Schweiz)	5-Substituierte 4-Azadibenzocyloheptene und Verfahren zu ihrer Herstellung
NL132137C (da) *	1963-04-24
US3717647A (en)	1971-04-09	1973-02-20	Schering Corp	Alpha-nicotinoyl phenylacetonitriles
GB1570500A (en) *	1976-01-02	1980-07-02	Sandoz Ltd	Anti-9,10-dihydro-4-(1-methyl-4-piperidylidene)-4h-benzo(4,5) cyclohepta (1,2-b)thiophen-10(9h)-one oxime
US4355036A (en) *	1980-06-19	1982-10-19	Schering Corporation	Tricyclic-substituted piperidine antihistamines
US4282233B1 (en) *	1980-06-19	2000-09-05	Schering Corp	Antihistaminic 11-(4-piperidylidene)-5h-benzoÄ5,6Ü-cyclohepta-Ä1,2Ü-pyridines
HU194864B (en) *	1984-02-15	1988-03-28	Schering Corp	Process for production of 8-chlor-6,11-dihydro-11-(4-piperidilidene)-5h-benzo (5,6)-cyclo-hepta (1,2-b) pyridine and its salts
DE3677842D1 (de) *	1985-05-13	1991-04-11	Schering Corp	Verfahren zur herstellung von piperidyliden-dihydrodibenzo(a,d)zykloheptenen und deren azoderivate, so hergestellte verbindungen und ihre anwendung zur vorbereitung von heilmitteln.
US4826853A (en) *	1986-10-31	1989-05-02	Schering Corporation	6,11-Dihydro-11-(N-substituted-4-piperidylidene)-5H-benzo(5,6)cyclohepta(1,2-B)pyridines and compositions and methods of use

1987
- 1987-04-28 US US07/043,409 patent/US4804666A/en not_active Expired - Lifetime
- 1987-10-21 AR AR87309067A patent/AR246520A1/es active
- 1987-10-21 IL IL8423587A patent/IL84235A/en not_active IP Right Cessation
- 1987-10-21 NZ NZ222253A patent/NZ222253A/xx unknown
- 1987-10-22 IE IE283987A patent/IE61740B1/en not_active IP Right Cessation
- 1987-10-22 PH PH35970A patent/PH26157A/en unknown
- 1987-10-22 EP EP87309349A patent/EP0288640B1/en not_active Expired - Lifetime
- 1987-10-22 ES ES87309349T patent/ES2043665T3/es not_active Expired - Lifetime
- 1987-10-22 JP JP63500439A patent/JPH0780870B2/ja not_active Expired - Fee Related
- 1987-10-22 WO PCT/US1987/002689 patent/WO1988008423A1/en active IP Right Grant
- 1987-10-22 PT PT85975A patent/PT85975B/pt not_active IP Right Cessation
- 1987-10-22 DE DE8787309349T patent/DE3781679T2/de not_active Expired - Fee Related
- 1987-10-22 CA CA000549987A patent/CA1332172C/en not_active Expired - Fee Related
- 1987-10-22 HU HU88308A patent/HU202520B/hu not_active IP Right Cessation
- 1987-10-22 AU AU10465/88A patent/AU612339B2/en not_active Ceased
- 1987-10-22 AT AT87309349T patent/ATE80394T1/de not_active IP Right Cessation
1988
- 1988-12-28 KR KR88701743A patent/KR960009426B1/ko not_active IP Right Cessation
1989
- 1989-10-24 FI FI895034A patent/FI96858C/fi not_active IP Right Cessation
- 1989-10-30 DK DK540789A patent/DK540789A/da not_active Application Discontinuation
1992
- 1992-06-24 MX MX9203282A patent/MX9203282A/es unknown
- 1992-12-09 GR GR920402839T patent/GR3006483T3/el unknown
1995
- 1995-08-24 HK HK135595A patent/HK135595A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
IL84235A0 (en)	1988-03-31
CA1332172C (en)	1994-09-27
KR890700583A (ko)	1989-04-25
AU612339B2 (en)	1991-07-11
DE3781679T2 (de)	1993-01-28
IL84235A (en)	1994-10-21
PT85975B (pt)	1992-07-31
AU1046588A (en)	1988-12-02
KR960009426B1 (en)	1996-07-19
EP0288640A1 (en)	1988-11-02
EP0288640B1 (en)	1992-09-09
DK540789D0 (da)	1989-10-30
IE872839L (en)	1988-10-28
PT85975A (en)	1987-11-01
GR3006483T3 (da)	1993-06-21
JPH02503909A (ja)	1990-11-15
DK540789A (da)	1989-10-30
HU202520B (en)	1991-03-28
NZ222253A (en)	1990-08-28
DE3781679D1 (de)	1992-10-15
FI96858C (fi)	1996-09-10
FI96858B (fi)	1996-05-31
JPH0780870B2 (ja)	1995-08-30
MX9203282A (es)	1992-07-01
US4804666A (en)	1989-02-14
FI895034A0 (fi)	1989-10-24
HK135595A (en)	1995-09-01
ES2043665T3 (es)	1994-01-01
AR246520A1 (es)	1994-08-31
WO1988008423A1 (en)	1988-11-03
ATE80394T1 (de)	1992-09-15
IE61740B1 (en)	1994-11-30

Publication	Publication Date	Title
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CA2053903C (en)	1999-03-30	Heterocyclic n-oxide derivatives of substituted benzo[5,6]cycloheptapyridines, compositions and methods of use
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IE49077B1 (en)	1985-07-24	5-(4-pyridyl)-6-(4-fluorophenyl)-2,3-dihydroimidazo(2,1-b)thiazole,process for its preparation and medical composition
IE912124A1 (en)	1992-01-01	Bis-benzo or benzopyrido cyclohepta piperidene, piperidylidene and piperazine compounds, compositions and methods of use
EP0586560A1 (en)	1994-03-16	Novel benzopyrido piperidylidene compounds, compositions, methods of manufacture and methods of use
US5430032A (en)	1995-07-04	Benzopyrido piperidylidene compounds, compositions, methods of manufacture and methods of use
EP0552245A1 (en)	1993-07-28	Bis-benzo cyclohepta piperidylidene, piperidine and piperazine compounds, compositions and methods of use
EP0642514B1 (en)	1997-05-21	Bridged bis-aryl carbinol derivatives, compositions and methods of use
US3408353A (en)	1968-10-29	1, 3, 4, 9b-tetrahydro-2h-indeno(1, 2-c)pyridine derivatives
KR840000077B1 (ko)	1984-02-08	10,11-디하이드로-5H-디벤조[a, d]사이클로 헵텐-5, 10-이민의 제조방법.
US3816438A (en)	1974-06-11	2h(1)-benzothiepino(5,4-c)-pyrazoles and(1)-benzothiopyrano(4,3-c)-pyrazoles
US3843664A (en)	1974-10-22	Substituted naphtho pyrazoles
US3391136A (en)	1968-07-02	3-chloro-11-(upsilan-dimethylaminopropylidene)-5, 6-dihydromorphanthridine and derivatives
CZ397191A3 (cs)	1994-07-13	Pyrrolo/l,2-a/imidazolové a pyrrolo/l,2-a/ pyridinové deriváty a farmaceutické prostředky sjejich obsahem