JPS6353984B2 - - Google Patents

Info

Publication number: JPS6353984B2
Authority: JP; Japan
Prior art keywords: acid; group; general formula; reaction; formula
Prior art date: 1980-11-18
Legal status (The legal status 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 status listed.): Expired

Application number

JP16290980A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5785346A (en

Inventor

Kanji Noda

Akira Nakagawa

Toshiharu Motomura

Masayoshi Tsuji

Juji Shimozono

Hiroyuki Ide

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hisamitsu Pharmaceutical Co Inc

Original Assignee

Hisamitsu Pharmaceutical Co Inc

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.)

1980-11-18

Filing date

1980-11-18

Publication date

1988-10-26

1980-11-18 Application filed by Hisamitsu Pharmaceutical Co Inc filed Critical Hisamitsu Pharmaceutical Co Inc

1980-11-18 Priority to JP16290980A priority Critical patent/JPS5785346A/ja

1982-05-28 Publication of JPS5785346A publication Critical patent/JPS5785346A/ja

1988-10-26 Publication of JPS6353984B2 publication Critical patent/JPS6353984B2/ja

Status Granted legal-status Critical Current

Links

150000005379 cyclohexanecarboxylic acid derivatives Chemical class 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
238000000862 absorption spectrum Methods 0.000 description 8
239000013078 crystal Substances 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 8
238000001819 mass spectrum Methods 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
-1 etc.) Chemical group 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000010438 heat treatment Methods 0.000 description 5
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 5
GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 5
239000003960 organic solvent Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
229960000401 tranexamic acid Drugs 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000003171 anti-complementary effect Effects 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
230000000767 anti-ulcer Effects 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229940012957 plasmin Drugs 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UAFHRUBCOQPFFM-UHFFFAOYSA-N 1-(aminomethyl)cyclohexane-1-carboxylic acid Chemical compound NCC1(C(O)=O)CCCCC1 UAFHRUBCOQPFFM-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
OHIRZNAJMCASJT-AULYBMBSSA-N C1C[C@@H](C(=O)O)CC[C@@H]1CN=CC1=CC=C(Cl)C=C1 Chemical compound C1C[C@@H](C(=O)O)CC[C@@H]1CN=CC1=CC=C(Cl)C=C1 OHIRZNAJMCASJT-AULYBMBSSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000027932 Collagen disease Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
QVYYEGRMCQYDSE-HDJSIYSDSA-N OC(=O)[C@H]1CC[C@H](CN=Cc2ccccc2)CC1 Chemical compound OC(=O)[C@H]1CC[C@H](CN=Cc2ccccc2)CC1 QVYYEGRMCQYDSE-HDJSIYSDSA-N 0.000 description 1
XSZOIIALDRPZQP-HDJSIYSDSA-N OC([C@H]1CC[C@H](CNCC2=CC=CC=C2)CC1)=O Chemical compound OC([C@H]1CC[C@H](CNCC2=CC=CC=C2)CC1)=O XSZOIIALDRPZQP-HDJSIYSDSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
GYDJEQRTZSCIOI-UHFFFAOYSA-N Tranexamic acid Chemical compound NCC1CCC(C(O)=O)CC1 GYDJEQRTZSCIOI-UHFFFAOYSA-N 0.000 description 1
ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
230000003627 anti-cholesterol Effects 0.000 description 1
230000002391 anti-complement effect Effects 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
238000000034 method Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
201000008383 nephritis Diseases 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
AAZYNPCMLRQUHI-UHFFFAOYSA-N propan-2-one;2-propan-2-yloxypropane Chemical compound CC(C)=O.CC(C)OC(C)C AAZYNPCMLRQUHI-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP16290980A 1980-11-18 1980-11-18 Cyclohexanecarboxylic acid derivative Granted JPS5785346A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP16290980A JPS5785346A (en)	1980-11-18	1980-11-18	Cyclohexanecarboxylic acid derivative

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP16290980A JPS5785346A (en)	1980-11-18	1980-11-18	Cyclohexanecarboxylic acid derivative

Publications (2)

Publication Number	Publication Date
JPS5785346A JPS5785346A (en)	1982-05-28
JPS6353984B2 true JPS6353984B2 (fi)	1988-10-26

Family

ID=15763526

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP16290980A Granted JPS5785346A (en)	1980-11-18	1980-11-18	Cyclohexanecarboxylic acid derivative

Country Status (1)

Country	Link
JP (1)	JPS5785346A (fi)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0522215U (ja) *	1991-09-02	1993-03-23	本田技研工業株式会社	車外配管の保持構造
USRE48565E1 (en)	1981-11-03	2021-05-18	Personalized Media Communications LLC	Providing a subscriber specific solution in a computer network

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS60163813A (ja) *	1984-02-04	1985-08-26	Morishita Jintan Kk	抗プラスミン薬
SI1879877T1 (sl)	2005-05-03	2013-02-28	Ranbaxy Laboratories Limited	Protimikrobna sredstva
JP2009533315A (ja) *	2006-04-10	2009-09-17	ランバクシーラボラトリーズリミテッド	抗菌剤

1980
- 1980-11-18 JP JP16290980A patent/JPS5785346A/ja active Granted

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
USRE48565E1 (en)	1981-11-03	2021-05-18	Personalized Media Communications LLC	Providing a subscriber specific solution in a computer network
JPH0522215U (ja) *	1991-09-02	1993-03-23	本田技研工業株式会社	車外配管の保持構造

Also Published As

Publication number	Publication date
JPS5785346A (en)	1982-05-28

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DE3834204C2 (fi)	1992-04-23
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JP2001505198A (ja)	2001-04-17	Ｐｄｅ阻害剤としての置換ジヒドロベンゾフラン
JPS6033114B2 (ja)	1985-08-01	１，２−ベンズイソキサゾ−ル誘導体
JPH01301661A (ja)	1989-12-05	新規ピリジル誘導体
US4977162A (en)	1990-12-11	Quinolinyl-chromone derivatives and use for treatment of hypersensitive ailments
JPS6353984B2 (fi)	1988-10-26
JPH07505394A (ja)	1995-06-15	橋渡しビスアリールカルビノール誘導体，組成物および使用法
JPH0673012A (ja)	1994-03-15	４−イミノキノリン、その製法およびその使用
JPS628117B2 (fi)	1987-02-20
JPS62277392A (ja)	1987-12-02	スルフエンアミド誘導体およびその製造法
JPH0559117B2 (fi)	1993-08-30
JPS5849369A (ja)	1983-03-23	新規のイミダゾール化合物
CA1078395A (en)	1980-05-27	Anti-inflammatory 1-oxo-isoindoline derivatives and processes for their preparation
JPH01203351A (ja)	1989-08-16	１，４−ジヒドロキシナフタレン誘導体および医薬
JPS6127977A (ja)	1986-02-07	４，５‐ジヒドロ‐３，３‐ジフエニル‐４‐ヒドロカルビルアミノメチルフラン‐２（３ｈ）‐オン
SARGENT	1954	THE SYNTHESIS OF 1-ETHYL-, 2-ETHYL-, 3-ETHYL-AND 4-ETHYL-ACRIDINE1
JPH01121274A (ja)	1989-05-12	２−置換シクロヘプトイミダゾール誘導体、抗潰瘍剤並びにその製法
JPS5993080A (ja)	1984-05-29	１，５−ナフチリジンカルボン酸誘導体
JPH02270868A (ja)	1990-11-05	抗炎症性１―ヘテロアリール―３―アシル―２―オキシンドール類
JPS6346736B2 (fi)	1988-09-19
JPS6026794B2 (ja)	1985-06-25	２−アミノクロモン−３−カルボキサアルデヒド誘導体およびその製造法
JPS59190988A (ja)	1984-10-29	１，３−ベンゾジオキサン誘導体およびその製造法

JPS6353984B2 - - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=15763526

Family Applications (1)

Country Status (1)

Cited By (2)

Families Citing this family (3)

Cited By (2)

Also Published As

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